- Annulation-retro-Claisen cascade of bifunctional peroxides for the synthesis of lactone natural products
-
A new and highly efficient annulation-retro-Claisen cascade, which involves the [4 + 1] or [5 + 1] annulation of α-benzoylacetates with bielectrophilic peroxides and a subsequent debenzoylation process under mild basic conditions, has been developed for the rapid construction of valuable tetrahydrofuran- and dihydropyran-2-carboxylates in good yields. By employing the new reaction, the unified total synthesis of γ- and δ-lactone natural products such as (±)-tanikolide, (±)-goniothalamins, (±)-7-epi-goniodiol, and (±)-plakolide A has been accomplished in 4-7 steps.
- Hu, Lin,Li, Jialin,Li, Xuemin,Xu, Qianlan
-
supporting information
p. 274 - 277
(2022/01/03)
-
- Total Synthesis of (R)-Argentilactone and (R)-Goniothalamin Using a Free-Radical Photoredox Approach to α,β-Unsaturated δ-Lactones
-
α,β-Unsaturated δ-lactones are structural motifs found in diverse pharmacologically active natural products. In fact, the unsaturated lactone is often responsible for the biological activity. Herein, we report a new approach for the syntheses of (R)-argentilactone and (R)- goniothalamin based on a photoredox intermolecular iodolactonization mediated by a photoredox process. This new approach, already employed in our research group, stands as a new methodology to achieve several natural products containing α,β-Unsaturated δ-lactones.
- Fuentes-Pantoja, Francisco J.,Cordero-Vargas, Alejandro
-
supporting information
p. 4433 - 4439
(2021/08/20)
-
- Synthesis and cytotoxic activities of goniothalamins and derivatives
-
Substituted goniothalamins containing cyclopropane-groups were efficiently prepared in high yields and good selectivity. Antiproliferative activity was measured on three human cancer cell lines (A549, MCF-7, HBL-100), to show which of the structural elements of goniothalamins is mandatory for cytotoxicity. We found that the configuration of the stereogenic centre of the δ-lactone plays an important role for cytotoxicity. In our studies only (R)-configured goniothalamins showed antiproliferative activity, whereby (R)-configuration accords to natural goniothalamin (R)-1. Additionally, the δ-lactone needs to be unsaturated whereas our results show that the vinylic double bond is not mandatory for cytotoxicity. Furthermore, with a two-fold in vitro and in vivo strategy, we determined the inhibitory effect of the compounds to the yeast protein Pdr5. Here, we clearly demonstrate that the configuration seems to be of minor influence, only, while the nature of the substituent of the phenyl ring is of prime importance.
- Weber, Anja,D?hl, Katja,Sachs, Julia,Nordschild, Anja C.M.,Schr?der, Dennis,Kulik, Andrea,Fischer, Thomas,Schmitt, Lutz,Teusch, Nicole,Pietruszka, J?rg
-
p. 6115 - 6125
(2017/09/30)
-
- First total synthesis of the highly potent antitumor lactones 8-chlorogoniodiol and parvistone A: Exploiting a bioinspired late-stage epoxide ring-opening
-
The first protecting group-free total syntheses of the highly potent antitumor chlorinated styryllactone secondary metabolites 8-chlorogoniodiol, parvistone A, and one analogue 8-epi-parvistone A, have been accomplished from commercially available trans-cinnamaldehyde in five steps with high overall yields. The chlorine-bearing stereogenic center of these silent secondary metabolites was introduced via a bioinspired late-stage regioselective epoxide ring-opening strategy. Maruoka asymmetric allylation, acrylation, ring-closing metathesis and asymmetric epoxidation, greatly facilitate the synthesis of the key intermediates goniothalamin oxide and (6S,7S,8S)-isogoniothalamin oxide.
- Ramesh, Perla,Narasimha Reddy, Yarram,Narendar Reddy, Thatikonda,Srinivasu, Navuluri
-
p. 246 - 249
(2017/02/15)
-
- Biosynthesis-Inspired Total Synthesis of Bioactive Styryllactones (+)-Goniodiol, (6S,7S,8S)-Goniodiol, (-)-Parvistone D, and (+)-Parvistone e
-
A protecting-group-free total synthesis of (+)-goniodiol (1), (6S,7S,8S)-goniodiol (2), (-)-parvistone D (4), and (+)-parvistone E (6) was efficiently achieved in five steps from commercially available trans-cinnamaldehyde with high overall yields (72-75%). The synthesis strategy was inspired from the proposed biosynthesis pathway of styryllactones. Key transformations of the strategy include a one-pot conversion of goniothalamin oxide to goniodiol or 9-deoxygoniopypyrone in aqueous media, stereoselective epoxidation, ring-closing metathesis, and stereoselective Maruoka allylation. The route is amenable to synthesis of various analogues for biological evaluation.
- Ramesh, Perla,Rao, Tadikamalla P.
-
p. 2060 - 2065
(2016/09/09)
-
- Stereoselective synthesis of the non-lactonic portion of (Z)-cryptofolione and approaches towards its conversion to (Z)-cryptofolione
-
The stereoselective synthesis of the non-lactonic part of the natural G2 checkpoint inhibitor, (Z)-cryptofolione, has been accomplished. Butane-1,4-diol was used as the starting material, and the stereogenic centers were generated through L-proline-catalyzed α-aminoxylation and Maruoka asymmetric allylation. We attempted to convert this non-lactonic moiety to (Z)-cryptofolione via olefin cross-metathesis reaction, but by this approach another naturally occurring lactonic compound, goniothalamin, was obtained.
- Nagendra, Siddavatam,Krishna Reddy, Vanka,Das, Biswanath
-
p. 520 - 526
(2015/04/27)
-
- Total synthesis of cryptomoscatone F1 through an asymmetric aldol approach
-
A stereoselective total synthesis of naturally occurring styryl lactone, cryptomoscatone F1 is described. A Mukaiyama asymmetric aldol reaction, Brown's asymmetric allylation, Maruoka asymmetric allylation, and cross metathesis were used as the key steps.
- Ramesh, Perla,Raju, Atla,Fadnavis, Nitin W.
-
p. 1251 - 1255
(2015/11/09)
-
- Enantiomerically pure allylboronic esters as versatile reagents in the enantioselective synthesis of dihydro-α-pyrone-containing natural products
-
A short and efficient enantio- and diastereoselective synthesis of different representatives from the class of dihydro-α-pyrone natural products, including both enantiomers of goniothalamin, massoia lactone, parasorbic acid, and some derivatives is presented. It is based on the application of enantiopure α-chiral allylboronic esters in allyl additions. Georg Thieme Verlag Stuttgart New York.
- Bartlett, Sean,Boese, Dietrich,Ghori, Daniel,Mechsner, Bastian,Pietruszka, Joerg
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p. 1106 - 1114
(2013/05/21)
-
- Design, synthesis, in vitro cytotoxicity evaluation and structure-activity relationship of Goniothalamin analogs
-
A series of six/five member (E/Z)-Goniothalamin analogs were synthesized from commercially available (3,4-dihydro-2H-pyran-2-yl)methanol/5- (hydroxymethyl)dihydrofuran-2(3H)-one in three steps with good to moderate overall yields and their cytotoxicity against lymphoblastic leukemic T cell line (Jurkat E6.1) have been evaluated. Among the synthesized analogs, (Z)-Goniothalamin appeared to be the most active in cytotoxicity (IC 50 = 12 μM). Structure-activity relationship study indicates that introducing substituent in phenyl ring or replacing phenyl ring by pyridine/naphthalene, or decreasing the ring size of lactones (from six to five member) do not increase the cytotoxicity.
- Mohideen, Mazlin,Zulkepli, Suraya,Nik-Salleh, Nik-Salmah,Zulkefeli, Mohd,Weber, Jean-Frédéric Faizal Abdullah,Rahman, A. F. M. Motiur
-
p. 812 - 831
(2013/07/26)
-
- Alcohol dehydrogenase-catalyzed synthesis of enantiomerically pure δ-lactones as versatile intermediates for natural product synthesis
-
Starting from ethyl 4-bromobutyrate, the chemoenzymatic synthesis of 6-vinyl-tetrahydro-pyran-2-one has been accomplished. A screening of a number of available alcohol dehydrogenases and intense optimization of reaction parameters enabled us to establish an efficient synthesis of either enantiomer of the vinyllactone with excellent enantiomeric excess (>99%). The scope of possible applications of enantiopure vinyllactones has been verified by subjection to cross-metathesis resulting in the total synthesis of the insect pheromone (S)-5-hexadecanolide and the cytotoxic styryllactone goniothalamine as well as derivatives thereof. Copyright
- Fischer, Thomas,Pietruszka, Joerg
-
p. 2521 - 2530,10
(2020/08/31)
-
- Stereoselective total synthesis of (+)-cryptofolione and (+)-goniothalamin
-
The stereoselective total synthesis of two naturally occurring α-pyrone derivatives (+)-cryptofolione and (+)-goniothalamin has been accomplished via a common intermediate. The synthetic sequence involves the asymmetric reduction of a propargyl ketone and olefin cross-metathesis as the key reactions.
- Das, Biswanath,Nagendra, Siddavatam,Reddy, Cheruku Ravindra
-
p. 1249 - 1254
(2011/10/19)
-
- The cytotoxic styryl lactone goniothalamin is an inhibitor of nucleocytoplasmic transport
-
An in vivo nuclear export assay (immunostaining of Rio2 in HeLa cells) demonstrated that (R)-goniothalamin is an inhibitor of nucleocytoplasmic transport above 500 nM, which was rationalized also by molecular modeling. The cytotoxic styryl lactone natural product was prepared via an enantioselective Cr(III) catalyzed hetero Diels-Alder reaction and a Sonogashira coupling. A series of analogs was synthesized and only the oxidized goniothalamin derivative featuring an alkyne spacer was found active. Unsaturated lactones of natural origin other than leptomycin (LMB) are thus suggested to operate via a similar mechanism targeting the CRM1 nuclear receptor.
- Wach, Jean-Yves,Güttinger, Stephan,Kutay, Ulrike,Gademann, Karl
-
supporting information; experimental part
p. 2843 - 2846
(2010/07/16)
-
- Stereoselective approaches to the total synthesis of (6R,4′S, 6′R)-cryptofolione
-
Total syntheses of cryptofolione were accomplished by two different routes via a common intermediate that underwent a cross-metathesis (CM) reaction with a vinyl lactone. The intermediate was prepared by coupling of an acyl anion equivalent with a chiral allyl epoxide synthon, or by Prins cyclization of a trans-cinnamaldehyde with a chiral homoallylic alcohol. Goniothalamin was obtained as a cross-metathesis product of the diacetate and vinyl lactone. Georg Thieme Verlag Stuttgart.
- Sabitha, Gowravaram,Reddy, S. Siva Sankara,Reddy, D. Vasudeva,Bhaskar, Vangala,Yadav, Jhillu S.
-
experimental part
p. 3453 - 3460
(2010/11/20)
-
- One-pot hydrosilylation-RCM-protodesilylation: Application to the synthesis of ω-alkenyl α,β-unsaturated lactones
-
A simple and efficient one-pot procedure has been developed for the synthesis of α,β-unsaturated lactones bearing a pendant E-olefin. This new methodology, which features a hydrosilylation, a ring-closing metathesis (RCM) and a protodesilylation reaction,
- Bressy, Cyril,Bargiggia, Frédéric,Guyonnet, Mathieu,Arseniyadis, Stellios,Cossy, Janine
-
experimental part
p. 565 - 568
(2009/07/10)
-
- De novo asymmetric syntheses of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin using asymmetric allylations
-
A highly enantio- and diastereoselective approach to either enantiomer of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin oxide has been developed from achiral cinnamyl alcohol or cinnamaldehyde. The asymmetry of the synthesis wa
- Harsh, Philip,O'Doherty, George A.
-
experimental part
p. 5051 - 5055
(2009/12/01)
-
- A concise enantioselective strategy to (+)-(R)-goniothalamin and (+)-(R)-goniothalamin oxide by employing hydrolytic kinetic resolution and ring-closing metathesis as key steps
-
An efficient and general strategy to (R)-goniothalamin and (R)-goniothalamin oxide is described by using Jacobsen's hydrolytic kinetic resolution of racemic epoxide and ring-closing metathesis (RCM) as key steps, which provided a rapid access to these natural products that display a fascinating array of biological activity. (R)-Goniothalamin oxide was prepared in high yield and diastereomeric excess under various epoxidation conditions. Georg Thieme Verlag Stuttgart.
- Bose, D. Subhas,Reddy, A. V. Narsimha,Srikanth, Bingi
-
body text
p. 2323 - 2326
(2009/04/04)
-
- Application of the Cosford cross-coupling protocol for the stereoselective synthesis of (R)-(+)-goniothalamin, (R)-(+)-kavain and (S)-(+)-7,8-dihydrokavain
-
An efficient and versatile synthetic method has been developed and utilized for the stereoselective synthesis of (R)-(+)-goniothalamin 1, (R)-(+)-kavain 2 and (S)-(+)-7,8-dihydrokavain 3. Application of the Cosford protocol and direct conversion of aldehydes to β-keto-esters are the key steps in our approach.
- Sabitha, Gowravaram,Sudhakar,Yadav
-
p. 8599 - 8602
(2007/10/03)
-
- α,β-unsaturated δ-lactones from copper-catalyzed asymmetric vinylogous mukaiyama reactions of aldehydes: Scope and mechanistic insights
-
A direct regio-, diastereo-, and enantiocontrolled access to α,β-unsaturated δ-lactones is described, based on the reaction of a silyl dienolate and an aldehyde in the presence of 10% of Carreira's catalyst. The scope and limitations of this reaction, as well as mechanistic insights concerning the reactivity of an allyl copper species, are discussed.
- Bazan-Tejeda, Belen,Bluet, Guillaume,Broustal, Garance,Campagne, Jean-Marc
-
p. 8358 - 8366
(2007/10/03)
-
- Total synthesis of (R)-(+)-goniothalamin and (R)-(+)-goniothalamin oxide: first application of the sulfoxide-modified Julia olefination in total synthesis
-
A short and efficient synthesis of (R)-(+)-goniothalamin 1 and (R)-(+)-goniothalamin oxide 2 is described. During this approach, the sulfoxide-modified Julia olefination was used as a key step to connect aldehyde 5 to sulfoxide 6. The desired styryl-containing adduct is obtained in good yield and with excellent E/Z selectivity.
- Pospí?il, Ji?í,Markó, István E.
-
p. 5933 - 5937
(2007/10/03)
-
- (R)-Goniothalamin: Total syntheses and cytotoxic activity against cancer cell lines
-
The total syntheses of (R)-goniothalamin (1), a styryl lactone isolated from several Goniothalamus species, via catalytic asymmetric allylation of α-benzyloxyacetaldehyde (2), followed by ring-closing metathesis and Wittig olefination and via catalytic asymmetric allylation of trans-cinnamaldehyde (12), followed by ring-closing metathesis are reported. The antiproliferative activities of (R)-1 and its Z-isomer 10 as well as of the synthetic dihydropyranone intermediates 7 and 8 against eight different cancer cell lines are also described.
- De Fatima, Angelo,Kohn, Luciana Konecny,Antonio, Marcia Aparecida,De Carvalho, Joao Ernesto,Pilli, Ronaldo Aloise
-
p. 2927 - 2933
(2007/10/03)
-
- Synthesis of (+)-goniothalamin and its enantiomer by combination of lipase catalyzed resolution and alkene metathesis
-
(+)-Goniothalamin has been synthesized by lipase catalyzed resolution of (1E)-1-phenylhexa-1,5-dien-3-ol using vinyl acrylate as acyl donor followed by ring closing metathesis of the formed (1R)-1-[(E)-2-phenylvinyl]but-3-enyl acrylate. The unreacted alcohol from the resolution, (1E,3S)-1-phenylhexa-1,5- dien-3-ol, was esterified non-enzymatically, and used for synthesis of (-)-goniothalamin.
- Sundby, Eirik,Perk, Lars,Anthonsen, Thorleif,Aasen, Arne J?rgen,Hansen, Trond Vidar
-
p. 521 - 524
(2007/10/03)
-
- Efficient synthesis of the styryllactones, (+)-goniothalamin, (+)-7-epi-goniodiol and (+)-9-deoxygoniopypyrone
-
An efficient synthesis of (+)-goniothalamin is described with aldehyde 4 as the key intermediate; the absolute configuration of (+)-7-epi-goniodiol was determined through its asymmetric synthesis from (+)-goniothalamin and, based on the conformation analysis of the four dihydroxylated isomers of (+)-goniothalamin, it can be concluded that the absolute configuration of the hydroxy at C8 determines the forms in nature.
- Liu, Zhi-Yu,Ji, Jian-Xin,Li, Bo-Gang
-
-
- Short and efficient chemoenzymatic synthesis of goniothalamin
-
A high-yielding three-step synthesis of goniothalamin involving an enzymatic kinetic resolution in the presence of vinyl acrylate followed by ring-closing metathesis is discussed.
- Gruttadauria, Michelangelo,Lo Meo, Paolo,Noto, Renato
-
-
- The β-lactone route to α,β-unsaturated δ-lactones. Total syntheses of (±)-goniothalamin and (-)-massoialactone
-
The HF-induced translactonization of 2′-silyloxy-3-trimethylsilyl-2- oxetanones, obtained through Lewis acid-promoted [2+2] cycloaddition between β-silyloxyaldehydes and trimethylsilylsilylketene, into α,β-unsaturated δ-lactones is applied to the syntheses of (±)-goniothalamin and (-)-massoialactone.
- Fournier, Lycia,Kocienski, Philip,Pons, Jean-Marc
-
p. 1659 - 1663
(2007/10/03)
-
- Total syntheses of (R)-argentilactone and (R)-goniothalamin via catalytic enantioselective allylation of aldehydes
-
The total syntheses of (R)-argentilactone (five steps, 25% overall yield) and (R)-goniothalamin (three steps, 61% overall yield) have been described through the enantioselective catalytic allylation of aldehydes (including a propargylic aldehyde) which provided a rapid access to these natural products that display very interesting biological activities.
- De Fátima, ?ngelo,Pilli, Ronaldo Aloise
-
p. 8721 - 8724
(2007/10/03)
-
- Facile enantioselective synthesis of 6R-(+)-goniothalamin and (6R, 7R, 8R)-(+)-goniothalamin oxide
-
Facile enantioselective total syntheses of 6R-(+)-goniothalamin 1 and (6R, 7R, 8R)-(+)-goniothalamin oxide 2 were achieved through the Sharpless kinetic resolution of racemic secondary 2- furylmethanol 3 in a short synthetic route.
- Peng, Xiaoshui,Li, Anpai,Shen, Hao,Wu, Tongxing,Pan, Xinfu
-
p. 330 - 332
(2007/10/03)
-
- A short and general approach to the synthesis of styryllactones: (+)-Goniodiol, its acetates and β-trifluoromethyl derivative, (+)-7-epi-Goniodiol and (+)-9-deoxygoniopypyrone
-
(+)-Goniodiol, its acetates and β-trifluoromethyl derivative, (+)-7-epi-Goniodiol and (+)-9-deoxygoniopypyrone, the representatives of styryllactones have been synthesized in a short and general way. The key steps involve the regioselective asymmetric dihydroxylation and the palladium-catalyzed cross-coupling of cyclic allylic carbonate with vinyltributylstannane.
- Chen, Jian,Lin, Guo-Qiang,Wang, Zhi-Min,Liu, Han-Quan
-
p. 1265 - 1268
(2007/10/03)
-
- Synthesis of unsaturated lactone moieties by asymmetric hetero Diels-Alder reactions with binaphthol-titanium complexes
-
Natural products like ratjadone and callystatin A contain an α,β-unsaturated lactone moiety which adds to the biological activity of these compounds. Here we report a rapid and practical access to lactone precursor 3 by an asymmetric hetero Diels-Alder reaction as the key step and its subsequent transformation into a suitable building block 4.
- Quitschalle, Monika,Christmann, Mathias,Bhatt, Ulhas,Kalesse, Markus
-
p. 1263 - 1265
(2007/10/03)
-
- Asymmetric synthesis of goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid via sequential allylboration-esterification ring-closing metathesis reactions
-
Acrylic esters of homoallylic alcohols prepared in 92-97% ee via the asymmetric allylboration of appropriate aldehydes with B- allyldiisopinocampheylborane, when refluxed in dichloromethane in the presence of 10 mol% of Grubbs' catalyst provided the natural enantiomers of (S)-(+)-parasorbic acid, (R)-(-)-massoia lactone, and (R)-(+)goniothalamin. (S)-(-)-Hexadecanolide was prepared by hydrogenating the corresponding lactenone synthesized using the above sequence. (C) 2000 Elsevier Science Ltd.
- Ramachandran, P. Veeraraghavan,Reddy, M. Venkat Ram,Brown, Herbert C.
-
p. 583 - 586
(2007/10/03)
-
- Stereochemistry of baker's yeast mediated reduction of α,β-unsaturated δ-lactones in the goniothalamin series
-
Baker's yeast reduction of racemic α,β-unsaturated δ-lactones 5, 6 and 7 proceeds with kinetic preference for the (S) enantiomers. The procedure allows the obtainment of enantiomerically pure (+)-(R)-goniothalamin 5.
- Fuganti,Pedrocchi-Fantoni,Sarra,Servi
-
p. 1135 - 1138
(2007/10/02)
-
- Use of 1,3-dioxin-4-ones and related compounds in synthesis. XLIV. Asymmetric aldol reaction of 4-trimethylsiloxy-6-methylene-1,3-dioxines: Use of tartaric acid-derived (acyloxy)borane complex as the catalyst
-
A novel enantioselective synthesis of 1,3-dioxin-4-ones having a 2-hydroxylated alkyl group at the 6-position has been accomplished by chiral tartaric acid-derived acylborane-mediated aldol condensation of the silyl enol ether derived from 6-methyl-derivatives of 1,3-dioxin-4-one with achiral aldehydes.
- Sato,Sunami,Sugita,Kaneko
-
p. 839 - 845
(2007/10/02)
-
- ENANTIOSELECTIVE SYNTHESIS OF 6-SUBSTITUTED 5,6-DIHYDRO-α-PYRANONES, (+)-GONIOTHALAMIN AND (-)-ARGENTILACTONE
-
An enantioselective synthesis of (+)-goniothalamin and (-)-argentilactone has been accomplished by employing the Wittig reactions of phosphoranes with the aldehyde (12) generated in situ by Swern oxidation of the alcohol (13) as a key step.
- Tsubuki, Masayoshi,Kanai, Kazuo,Honda, Toshio
-
p. 281 - 288
(2007/10/02)
-
- Stereocontrolled Route to the δ-Benzylidenemethyl-β-hydroxy-δ-lactone System Utilizing a New Chiral Epoxyacetylene Building Block
-
Stereocontrolled route to the δ-benzylidenemethyl-β-hydroxy-δ-lactone system has been developed utilizing a new epoxyacetylene building block prepared from optically active epichlorohydrin.The present synthesis allowed efficient construction of goniothalamin in natural and unnatural forms and its 3-hydroxy derivative having the essential anti-β/δ-stereochemistry for HMG Co-A reductase inhibition.
- Takano, Seiichi,Kamikubo, Takashi,Sugihara, Takumichi,Ogasawara, Kunio
-
p. 853 - 856
(2007/10/02)
-
- An Alternative Approach to Mevinic Acid Analogues from Methyl (3R)-(-)-3-Hydroxyhex-5-enoate and an Extension to Unambiguous Syntheses of (6R)-(+)- and (6S)-(-)-Goniothalamin
-
Ozonolysis of the 3-silyloxyhexenoate 12, derived from the yeast reduction product methyl (3R)-(-)-3-hydroxyhex-5-enoate 6 and having an enantiomeric enrichment of 78percent, followed by Wittig homologation and selenolactonization leads to the unsaturated mevinic acid analogues 17 and 18.Subsequent dehydration gives both enantiomers of the natural product goniothalamin 20 and 21.
- Bennett, Frank,Knight, David W.,Fenton, Garry
-
p. 519 - 523
(2007/10/02)
-
- Enantioselective Syntheses of (+)-Acetylphomalactone and (6R)-(+)-Goniothalamin from 2-Furylmethanols
-
Enantioselective syntheses of two 6-substituted 5,6-dihydro-2H-pyran-2-ones, (+)-acetylphomalactone and (6R)-(+)-goniothalamin, are described which use the kinetic resolution of racemic secondary 2-furylmethanols.
- Honda, Toshio,Kametani, Tetsuji,Kanai, Kazuo,Tatsuzaki, Yoko,Tsubuki, Masayoshi
-
p. 1733 - 1737
(2007/10/02)
-
- Intramolecular Nucleophilic Addition to Photochemically Generated Ketenes as a Versatile Route to Lactones and Lactams; Synthesis of a Mosquito Pheromone, Goniothalamin, Argentilactone, and the Streptomyces L-Factor
-
Photolysis of hydroxy-, dihydroxy- and amino-bicycloalkanones has been used as the key step in the synthesis of naturally occurring lactones including a mosquito pheromone, goniothalamin, argentilactone, and the Streptomyces L-factor, and of a γ-lactam.
- Rahman, Shahzad S.,Wakefield, Basil J.,Roberts, Stanley M.,Dowle, Michael D.
-
p. 303 - 304
(2007/10/02)
-
- A GENERAL APPROACH TO THE SYNTHESIS OF 5,6-DIHYDRO-2(2H)PYRANONES; SIMPLE SYNTHESIS OF α-PYRONE, (+/-)-ARGENTILACTONE AND (+/-)-GONIOTHALAMIN
-
Easily accessible dihydropyrans undergo oxidation with PDC/t-BuOOH to yield the corresponding 5,6-dihydro-2-(2H)-pyranones in good yield.The methodology is exemplified with the synthesis of α-pyrone, (+/-)-argentilactone and (+/-)-goniothalamin.
- Chidambaram, N.,Satyanarayana, K.,Chandrasekaran, S.
-
p. 2429 - 2432
(2007/10/02)
-
- SYNTHESIS OF THE 5,6-DIHYDRO-2-PYRONE MOIETY OF (+)-ANAMARIN
-
The α,β-unsaturated δ-lactone (+)-goniothalamin (18E) and its Z-isomer (18Z), which contain the lactonic moiety of (+)-anamarin (1), have been synthesized from the known 1,2-O-isopropylidene 3-deoxy-α-D-glucofuranose (7).In the key step, methyl 3,5-dideoxy-β-D-glucofuranuronate (15) was treated with benzylidenetriphenylphosphorane in dimethyl sulphoxide to give the E- and Z-β-hydroxy δ-lactones (17).These were then transformed into the 5,6-dihydro-2-pyrones (18), and also into the aldehyde (20), intended for use in a total synthesis of (+)-anamarin (1).
- Gillard, Frederic,Heissler, Denis,Riehl, Jean-Jacques
-
p. 2291 - 2296
(2007/10/02)
-
- SYNTHESES OF ARGENTILACTONE 11 AND GONIOTHALAMIN 15
-
Syntheses of (-)-(5R)-argentilactone 11 and (+)-(5R)-goniothalamin 15 are described starting from olefin 4.
- O'Connor, Brian,Just, George
-
p. 5201 - 5202
(2007/10/02)
-