𝔖 Bobbio Scriptorium
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Total synthesis of (±)-isoavenaciolide and (±)-avenaciolide

✍ Scribed by Steven D. Burke; Gregory J. Pacofsky; Anthony D. Piscopio

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
304 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

The antifungal mold metabolites isoavenaciolide (1 b) and avenaciolide (1~) have been synthesized in racemic form from a common precursor, a-methylene lactone 4. obtained via a glycolate ester enolate Claisen rearrangement.

We recently reported2 a total synthesis of the bislactone mold metabolite ethisolide (la)3a based upon the antithetic plan presented in eq. 1. The premise that the butenolide glycolate ester shown would give

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Stereo-divergent asymmetric total synthe
Stereo-divergent asymmetric total synthesis of avenaciolide and isoavenaciolide. Complete reversal of stereoselectivity in reduction of 2-vinyl aldols with / without trimethylsilyl directing group
✍ Keisuke Suzuki; Mayumi Miyazawa; Masato Shimazaki; Gen-ichi Tsuchihashi 📂 Article 📅 1986 🏛 Elsevier Science 🌐 French ⚖ 253 KB

## Stereo-divergent asymmetric total synthesis of avenaciolide and isoavenaciolide was achieved via 1.2-rearrangement of chiral epoxyalcohol derivatives. where complete reversal of stereoselectivity with / without the TMS-directing group in the reduction of Z-vinyl aldols was used as the key branc