- Biosynthesis-Inspired Total Synthesis of Bioactive Styryllactones (+)-Goniodiol, (6S,7S,8S)-Goniodiol, (-)-Parvistone D, and (+)-Parvistone e
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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.
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p. 2060 - 2065
(2016/09/09)
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- Tandem α-aminoxylation-allylation reaction based approach for the synthesis of goniothalesdiol A, leiocarpin A and (+)-goniodiol
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A short and efficient syntheses of goniothalesdiol A, leiocarpin A, and (+)-goniodiol are reported by a convergent strategy using tandem aminoxylation-allylation reaction as a key step starting from benzaldehyde.
- Sabitha, Gowravaram,Rammohan Reddy,Yadav
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scheme or table
p. 6550 - 6553
(2012/01/06)
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- An efficient total synthesis of (+)-goniodiol
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An efficient total synthesis of (+)-goniodiol was illustrated by using Carreira alkynylation and Sharpless asymmetric dihydroxylation as key steps. Georg Thieme Verlag Stuttgart New York.
- Sabitha, Gowravaram,Bhikshapathi,Ranjith,Ashwini,Yadav, Jhillu S.
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p. 821 - 825
(2011/04/25)
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- A concise enantioselective synthesis of (+)-goniodiol and (+)-8-methoxygoniodiol via Co-catalyzed HKR of anti-(2SR, 3RS)-3-methoxy-3- phenyl-1, 2-epoxypropane
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A short, enantioselective synthesis of (+)-goniodiol and (+)-8-methoxygoniodiol, cytotoxic styryllactones, has been achieved in high optical purities (99% ee). The strategy employs Co-catalyzed HKR of racemic anti-(2SR, 3RS)-3-methoxy-3-phenyl-1, 2-epoxypropane and Lewis acid-mediated diastereoselective allylation of aldehyde as chiral inducing key reactions.
- Kiran, I.N. Chaithanya,Reddy, R. Santhosh,Suryavanshi, Gurunath,Sudalai, Arumugam
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scheme or table
p. 438 - 440
(2011/03/18)
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- Stereoselective and facile total synthesis of (+)-goniodiol, a styryllactone from carbohydrates
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The stereoselective synthesis of (+)-goniodiol, a cytotoxic styryllactone, has been accomplished in 10 steps starting from inexpensive and readily available d-manitol and δ-gluconolactone involving the direct and straightforward reaction conditions of Gri
- Yadav, Jhillu Singh,Das, Saibal,Mishra, Anand Kumar
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experimental part
p. 2443 - 2447
(2011/02/22)
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- Stereoselective total synthesis of leiocarpin C and (+)-goniodiol
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Total syntheses of styryl lactones, leiocarpin C and (+)-goniodiol have been accomplished in a highly stereoselective manner. The key steps involved in these syntheses are the Chan alkyne reduction, Sharpless asymmetric dihydroxylation, Horner-Wadsworth-E
- Yadav,Krishna, V. Hari,Srilatha,Somaiah,Reddy, B. V. Subba
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experimental part
p. 3004 - 3012
(2010/10/21)
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- The first stereoselective and the total synthesis of Leiocarpin C and total synthesis of (+)-Goniodiol
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The synthesis of the styryl lactone Leiocarpin C has been achieved in a highly stereoselective manner using Jacobsen's kinetic resolution, Sharpless asymmetric epoxidation and Sharpless asymmetric dihydroxylation as key steps. This is the first total synthesis of Leiocarpin C, and thus establishes for the first time the absolute stereochemistry of this natural product.
- Yadav,Premalatha,Harshavardhan,Subba Reddy
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body text
p. 6765 - 6767
(2009/04/11)
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- Stereoselective synthesis of (+)-goniodiol, (+)-goniotriol, (-)-goniofupyrone, and (+)-altholactone using a catalytic asymmetric hetero-Diels-Alder/allylboration approach
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The stereoselective total synthesis of several members of the styryllactone family was achieved efficiently from common intermediate 8, prepared by a catalytic asymmetric inverse-electron-demand hetero-Diels-Alder/allylboration sequence. The transformatio
- Favre, Annaick,Carreaux, Francois,Deligny, Michael,Carboni, Bertrand
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experimental part
p. 4900 - 4907
(2009/06/06)
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- Syntheses of all stereoisomers of goniodiol from yeast-reduction products and their antimicrobiological activity
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All stereoisomers of goniodiol were synthesized from yeast-reduction products. The C-6 chiral centers were converted from the chiral centers of the yeast-reduction products. Stereoselective conversion of the alkene, which had been prepared from the yeast-reduction product, to glycol constructed the C-7 and C-8 stereochemistry. (+)-Goniodiol and 7-epi-(+)-goniodiol showed the highest antibacterial activity (MIC, 3.1 mM) against Yersinia intermedia.
- Yoshida, Takahiro,Yamauchi, Satoshi,Tago, Ryosuke,Maruyama, Masafumi,Akiyama, Koichi,Sugahara, Takuya,Kishida, Taro,Koba, Yojiro
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p. 2342 - 2352
(2008/12/23)
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- Total synthesis and cytotoxicity of (+)- and (-)-goniodiol and 6-epi-goniodiol. Construction of α,β-unsaturated lactones by ring-closing metathesis
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(+)-Goniodiol, a potent and selective cytotoxin, and (-)-6-epi-goniodiol, as well as their enantiomers, have been synthesized starting from cinnamyl alcohol. The key steps of the synthesis were Sharpless asymmetric epoxidation and cyclization of an acrylate derivative using ring-closing metathesis reaction. The cytotoxicity of both enantiomers of goniodiol and 6-epi-goniodiol against HL-60 cells was examined.
- Nakashima, Katsuyuki,Kikuchi, Naoki,Shirayama, Daisuke,Miki, Takuo,Ando, Kazuhiro,Sono, Masakazu,Suzuki, Shinya,Kawase, Masaki,Kondoh, Masuo,Sato, Masao,Tori, Motoo
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p. 387 - 394
(2008/02/11)
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- Facile stereoselective syntheses of goniodiol, 8-epi-goniodiol and 9-deoxygoniopypyrone
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Stereoselective syntheses of the bio-active styryllactones goniodiol and 9-deoxygoniopypyrone were accomplished from d-(-)-tartaric acid. The key step involves the elaboration of a γ-hydroxy butyramide to the styryllactones via high yielding stereoselecti
- Prasad, Kavirayani R.,Gholap, Shivajirao L.
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p. 4679 - 4682
(2008/03/12)
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- A highly enantioselective total synthesis of (+)-goniodiol
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A high-yielding enantioselective total synthesis of the bioactive styryllactone (+)-goniodiol has been realised, starting from readily available (S)-glycidol. A key step is an oxygen-to-carbon rearrangement of a silyl enol ether linked via an anomeric cen
- Tate, Edward W.,Dixon, Darren J.,Ley, Steven V.
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p. 1698 - 1706
(2008/02/11)
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- A concise synthesis of (+)-goniodiol using a catalytic hetero Diels-Alder/allylboration sequence
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A new short and efficient synthesis of (+)-goniodiol is reported using a catalytic asymmetric hetero Diels-Alder/allylboration sequence. Georg Thieme Verlag Stuttgart.
- Deligny, Michael,Carreaux, Fran?ois,Carboni, Bertrand
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p. 1462 - 1464
(2007/10/03)
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- A total synthesis of the styryllactone (+)-goniodiol from naphthalene
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The cytotoxic natural product (+)-goniodiol (1) has been prepared in twelve steps from the enantiomerically pure cis-dihydrocatechol (2), which is readily obtained by microbial oxidation of naphthalene. Elaboration of compound (2) involves an initial oxid
- Banwell, Martin G.,Coster, Mark J.,Edwards, Alison J.,Karunaratne, Ochitha P.,Smith, Jason A.,Welling, Lee L.,Willis, Anthony C.
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p. 585 - 595
(2007/10/03)
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- A short and general approach to the synthesis of styryllactones: (+)-Goniodiol, its acetates and β-trifluoromethyl derivative, (+)-7-epi-Goniodiol and (+)-9-deoxygoniopypyrone
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(+)-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
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p. 1265 - 1268
(2007/10/03)
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- A chemoenzymatic synthesis of the styryllactone (+)-goniodiol from naphthalene
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The enantiomerically pure cis-1,2-diol 2, which is obtained by microbial oxidation of naphthalene, has been converted, via a sequence of reactions including oxidative C-C bond cleavage, decarbonylation and ring-closing metathesis steps, into the natural p
- Banwell, Martin G.,Coster, Mark J.,Karunaratne, Ochitha P.,Smith, Jason A.
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p. 1622 - 1624
(2007/10/03)
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- Stereoselective syntheses of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone via alkoxyallylboration and ring-closing metathesis
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A convenient synthesis of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone has been developed via asymmetric alkoxyallylboration and ring-closing metathesis pathways.
- Ramachandran, P. Veeraraghavan,Chandra, J. Subash,Reddy, M. Venkat Ram
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p. 7547 - 7550
(2007/10/03)
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- Total synthesis of antitumor Goniothalamus styryllactones
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Synthesis of eight enantiopure styryllactones has been achieved from a common precursor: ethyl (2S, 3S, 4R)-4-(t-butyldimethylsilyloxy)-2,3- isopropylidenedioxy-4-phenylbutanoate 16, prepared in five steps and 65% yield from (R)-mandelic acid. Key elements for the synthesis of goniofufurone 3, goniopypyrone 4, goniobutenolides A and B (5, 6) and 7-epi-goniofufurone 7 were the introduction of the Z-acrylate moiety by a Julia coupling between 16 or its epimer in benzylic position and methyl 3-phenylsulfonyl orthopropionate 11 followed by a highly diastereoselective reduction of the resulting β-keto sulfone which sets up the last of the four contiguous asymmetric center. In the case of styryllactones 4 and 7, prior to the Julia coupling, the benzyl sterocenter of 16 was efficiently inverted by a Mitsunobu reaction. Goniodiol 1 and 9-deoxygoniopypyrone 2 were synthesized via an efficient coupling between the primary triflate derived from the common intermediate 16 or its epimer and Ghosez's sulfone 11 followed by lactonization and PhSO2H elimination. Goniodiol 1 has been efficiently converted to another styryllactone: isogoniothalamin epoxide 41. Addition of the Ghosez's sulfone to an epoxide derived from the enantiomer of 16 allowed a short synthesis of 8-epi-9-deoxygoniopypyrone 8, thereby establishing that its structure is the following: (1R, 5R, 7S, 8S)-8-hydroxy-7-phenyl-2,6- dioxabicyclo[3.3.1] nonan-3-one.
- Surivet, Jean-Philippe,Vatele, Jean-Michel
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p. 13011 - 13028
(2007/10/03)
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- Stereocontrolled syntheses of novel styryl lactones, (+)-goniodiol, (+)- goniotriol, (+)-8-acetylgoniotriol, (+)-goniofufurone, (+)-9- deoxygoniopypyrone, (+)-goniopypyrone, and (+)-altholactone from common intermediates and cytotoxicity of their congener
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Concise syntheses of (+)-goniodiol, (+)-goniotriol, (+)-8- acetylgoniotriol, (+)-goniofufurone, (+)-9-deoxygoniopypyrone, (+)- goniopypyrone, and (+)-altholactone and their congeners from chiral lactonic aldehydes 27 and 36 as common intermediates are des
- Tsubuki, Masayoshi,Kanai, Kazuo,Nagase, Hiromasa,Honda, Toshio
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p. 2493 - 2514
(2007/10/03)
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- A total synthesis of (+)-Goniodiol using an anomeric oxygen-to-carbon rearrangement
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A new route to (+)-Goniodiol 1, a potent and selective cytotoxin, is described, using a diastereoselective oxygen-to-carbon rearrangement of an anomerically linked silyl enol ether as the key step.
- Dixon, Darren J.,Ley, Steven V.,Tate, Edward W.
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p. 3125 - 3126
(2007/10/03)
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- A short and efficient total synthesis of the cytotoxic (+)-goniodiol and (+)-9-deoxygoniopypyrone
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(+)-Goniodiol 7 and (+)-9-deoxygoniopypyrone 8, belonging to the group of styryllactones, have been synthesized in five steps and 75% yield respectively from C4-esters 1a and 1b. The key step of these syntheses is a triflate-sulfone coupling which allowed a rapid construction of the backbone of the title compounds as well as the efficient installation of a masked Z- acrylate moiety.
- Surivet, Jean-Philippe,Vatele, Jean-Michel
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p. 7299 - 7300
(2007/10/03)
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- Stereoselective Syntheses of (+)-Goniotriol, (+)-8-Acetylgoniotriol, (+)-Goniodiol, (+)-9-Deoxygoniopypyrone, (+)-Altholactone, and (-)-Goniofupyrone
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The γ-lactone intermediate (-)-7, derived from (+)-tricarbonyl(η6-o-(trimethylsilyl)benzaldehyde)chromium(0) complex, was efficiently converted into the corresponding δ-lactone intermediate (-)-11. This second intermediate has been shown to be a versatile compound for stereoselective syntheses of natural styryllactones possessing a six-membered lactone moiety, isolated from Goniothalamus giganteus, by transforming it into (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniodiol, (+)-9-deoxygoniopypyrone, (+)-altholactone, and (-)-goniofupyrone.
- Mukai, Chisato,Hirai, Syuichi,Hanaoka, Miyoji
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p. 6619 - 6626
(2007/10/03)
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- Total synthesis of (+)-goniodiol
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Cytotoxic styryl lactone, (+)-goniodiol 1, was prepared in enantioenriched form (33 92%) in 15 steps from the α-(α'-alkoxyallenic) alcohol 5.
- Surivet, Jean-Philippe,Gore, Jacques,Vatele, Jean-Michael
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p. 371 - 374
(2007/10/03)
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- Enantioselective synthesis of (+)-goniodiol and of its naturally occurring acetylated analogs
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A novel route to enantioenriched (+)-goniodiol and its natural acetylated derivatives, potent cytotoxic compounds, is described. The main features of this synthesis are transfer of the asymmetric information of the scalemic allenic alcohol 5 to the α- and β- carbons through highly diastercoselective reactions and introduction of the α,β-unsaturated lactone moiety by the Ghosez' methodology.
- Surivet, Jean-Philippe,Gore, Jacques,Vatele, Jean-Michel
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p. 14877 - 14890
(2007/10/03)
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- Styrylpyrone Derivatives from Goniothalamus dolichocarpus
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Styrylpyrone derivatives (+)-goniothalamin (1), (+)-goniothalamin epoxide (2) and (-)-iso-5-deoxygoniopypyrone (4b), and the acetogenin (+)-annonacin (7) were bioactive compounds isolated from the stem bark of Goniothalamus dolichocarpus.The stereochemica
- Goh, S. H.,Ee, G. C. L.,Chuah, C. H.,Wei, Chen
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p. 199 - 206
(2007/10/02)
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- Goniodiol and 9-Deoxygoniopypyrone: Syntheses and Absolute Configurations
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The absolute configurations of natural goniodiol and 9-deoxygoniopypyrone are confirmed as 1 and 2 respectively by enantioselective syntheses starting from (2S,3R)-1,2-O-isopropylidene-3-(2-furyl)glycerol 6.
- Tsubuki, Masayoshi,Kanai, Kazuo,Honda, Toshio
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p. 1640 - 1641
(2007/10/02)
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