17303-67-2Relevant academic research and scientific papers
Annulation-retro-Claisen cascade of bifunctional peroxides for the synthesis of lactone natural products
Hu, Lin,Li, Jialin,Li, Xuemin,Xu, Qianlan
supporting information, p. 274 - 277 (2022/01/03)
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.
Total Synthesis of (R)-Argentilactone and (R)-Goniothalamin Using a Free-Radical Photoredox Approach to α,β-Unsaturated δ-Lactones
Fuentes-Pantoja, Francisco J.,Cordero-Vargas, Alejandro
, p. 4433 - 4439 (2021/08/20)
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.
Synthesis and cytotoxic activities of goniothalamins and derivatives
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)
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.
First total synthesis of the highly potent antitumor lactones 8-chlorogoniodiol and parvistone A: Exploiting a bioinspired late-stage epoxide ring-opening
Ramesh, Perla,Narasimha Reddy, Yarram,Narendar Reddy, Thatikonda,Srinivasu, Navuluri
, p. 246 - 249 (2017/02/15)
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.
Biosynthesis-Inspired Total Synthesis of Bioactive Styryllactones (+)-Goniodiol, (6S,7S,8S)-Goniodiol, (-)-Parvistone D, and (+)-Parvistone e
Ramesh, Perla,Rao, Tadikamalla P.
, p. 2060 - 2065 (2016/09/09)
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.
Stereoselective synthesis of the non-lactonic portion of (Z)-cryptofolione and approaches towards its conversion to (Z)-cryptofolione
Nagendra, Siddavatam,Krishna Reddy, Vanka,Das, Biswanath
, p. 520 - 526 (2015/04/27)
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.
Total synthesis of cryptomoscatone F1 through an asymmetric aldol approach
Ramesh, Perla,Raju, Atla,Fadnavis, Nitin W.
, p. 1251 - 1255 (2015/11/09)
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.
Design, synthesis, in vitro cytotoxicity evaluation and structure-activity relationship of Goniothalamin analogs
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)
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.
Enantiomerically pure allylboronic esters as versatile reagents in the enantioselective synthesis of dihydro-α-pyrone-containing natural products
Bartlett, Sean,Boese, Dietrich,Ghori, Daniel,Mechsner, Bastian,Pietruszka, Joerg
, p. 1106 - 1114 (2013/05/21)
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.
Alcohol dehydrogenase-catalyzed synthesis of enantiomerically pure δ-lactones as versatile intermediates for natural product synthesis
Fischer, Thomas,Pietruszka, Joerg
, p. 2521 - 2530,10 (2020/08/31)
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
