33644-09-6Relevant academic research and scientific papers
Total synthesis of (-)-isoavenaciolide
Santos, David,Ariza, Xavier,Garcia, Jordi,Lloyd-Williams, Paul,Martínez-Laporta, Agustín,Sánchez, Carolina
, p. 1519 - 1524 (2013)
An enantioselective approach to (-)-isoavenaciolide was achieved starting from 1-undecyn-3-ol. The synthesis relied upon the preparation of a chiral 4-silyloxy-2-alkenylborane by hydroboration of a protected 2,3-allenol and subsequent stereoselective addition to 2-thiophenecarboxaldehyde.
Short total syntheses of the avenaciolide family of natural products
Ainsua Martinez, Sandra,Gillard, Martin,Chany, Anne-Caroline,Burton, Jonathan W.
, p. 5012 - 5021 (2018/07/06)
The avenaciolide family of natural products are small α-methylene bis-γ-lactones that exhibit a wide variety of biological activities. Herein we report concise syntheses of five members of this family of natural products along with the synthesis of one no
Asymmetric sequential allylic transfer reaction for the synthesis of 2-(1-stannylvinyl)-1,3-diols: Concise synthesis of (-)-avenaciolide and (-)-isoavenaciolide
Yu, Chan-Mo,Youn, Jinsuop,Jung, Juyoung
, p. 1553 - 1556 (2007/10/03)
(Chemical Equation Presented) More adventures of tin-tin: The stereo-specific synthesis of 2-stannylvinyl-1,3-diols was achieved through a one-pot allylic transfer/distannation/allylic transfer reaction sequence (see scheme). The method was applied to the concise asymmetric syntheses of (-)-avenaciolide and (-)-isoavenaciolide.
Total Synthesis of Natural Bicyclic Lactones (+)-Dihydrocanadensolide, (±)-Avenociolide, and (±)-Isoavenociolide via Tungsten-π-Allyl Complexes
Chen, Ming-Jung,Narkunan, Kesavaram,Liu, Rai-Shung
, p. 8311 - 8318 (2007/10/03)
A synthetic method using tungsten-π-allyl compounds is developed for total syntheses of natural bislactones including (+)-dihydrocanadensaolide (2), (±)-avenociolide (3), and (±)-isoavenociolide (4). Syntheses of these natural compounds are based on a com
Highly Enantioselective Synthesis of Both Enantiomers of γ-Substituted Butenolides by Bakers' Yeast Reduction and Lipase-Catalyzed Hydrolysis. Total Synthesis of (3AS,6aS)-Ethisolide, Whisky Lactone, and (-)-Avenaciolide
Tsuboi, Sadao,Sakamoto, Jun-Ichi,Yamashita, Hiroshi,Sakai, Takashi,Utaka, Masanori
, p. 1102 - 1108 (2007/10/03)
Reduction of 3-chloro-4-oxoalkanoates 5 with bakers' yeast gave (4S)-3-chloro-4-hydroxyalkanoates, which were hydrolyzed and dehydrochlorinated to give (γS)-alkylbutenolides with >96% ee. Reduction of 5 with NaBH4 gave syn-3-chloro-4-hydroxyalkanoate 6. Asymmetric hydrolysis of syn-4-chloro-3-hydroxyalkanoate (±)-10 with lipase afforded (3R,4R)-6 and (3S,4S)-10 with high optical purities. Hydrolysis and dehydrochlorination of (3R,4R)-6 gave (γA)-alkylbutenolides with >85% ee. Total syntheses of (3aS,6aS)-ethisolide, whisky lactone, and (-)-avenaciolide from these butenolides are described.
An efficient method for total syntheses of avenaciolide and isoavenaciolide via tungsten-π-allyl complexes
Narkunan, Kesavaram,Liu, Rai-Shung
, p. 1521 - 1522 (2007/10/03)
Total syntheses of avenaciolide and isoavenaciolide were achieved in six and three steps respectively based on starting chloropropargyl derivatives; the key step in such syntheses involves intramolecular alkoxycarbonylation of tungsten-η1-propa
A new stereoselective synthesis of (-)-isoavenaciolide and (-)-avenaciolide
Rodriguez, Carmen M.,Martin, Tomas,Martin, Victor S.
, p. 8448 - 8452 (2007/10/03)
The synthesis of isoavenaciolide and avenaciolide in their natural enantiomeric forms are described. In both syntheses, α-(phenylthio)-β-[(methoxycarbonyl)methyl]-γ-lactones obtained by the base-induced cyclization of enantiomerically enriched γ-[(phenylthio)acyl] α,β-unsaturated esters were used as starting materials. In the isoavenaciolide synthesis the key step is the stereoselective hydroxylation of the enolate generated in the (methoxycarbonyl)methyl chain that permits the bis-lactonization by a double transesterification. The configuration in the quaternary center vicinal to the carbonyl group in the ring was critical in order to obtain successfully the α-methylene lactone. In avenaciolide, the stereoselective synthesis of the bis-lactone unit was performed taking advantage of the presence of the phenyl sulfide group which by previous activation was used as leaving group to obtain the fused ring by an intramolecular substitution utilizing the carboxylate of the β-substituent as nucleophile. In this case, the α-methylene lactone was obtained by previously reported methodology.
Synthesis of (±)-isoavenaciolide and of (±)-ethisolide from (±)-7-oxabicyclo|2.2.1|hept-5-en-2-one
Cossy, Janine,Ranaivosata, Jean-Luc,Bellosta, Veronique
, p. 629 - 638 (2007/10/03)
A short total synthesis of (±)-ethisolide and (±)-isoavenaciolide was accomplished from (±)-oxanorbornenone respectively in 11 and 12 steps, using a radical cyclization as a key step.
Synthesis of Ethisolide, Isoavenaciolide, and Avenaciolide
Burke, Steven D.,Pacofsky, Gregory J.,Piscopio, Anthony D.
, p. 2228 - 2235 (2007/10/02)
Syntheses of the trio of related mold metabolites ethisolide (1), isoavenaciolide (2), and avenaciolide (3) in racemic and optically active forms are described.Glycolate Claisen rearrangements governed by chelation control of enolate geometry and diastere
TOTAL SYNTHESIS OF (-)-ISOAVENACIOLIDE AND (-)-ETHISOLIDE
Wee, Andrew G. H.
, p. 5065 - 5076 (2007/10/02)
Natural isoavenaciolide and ethisolide were obtained from two bis-butyrolactone intermediates derived from a common bicyclic ester 8, prepared from D-ribose.
