A NEW STEREOSELECTIVE ROUTE TO γ-BUTYROLACTONES : ASYMMETRIC SYNTHESES OF (+)-trans-WHISKY AND (+)-trans-COGNAC LACTONES

Okiko MIYATA; Tetsuro SHINADA; Nanako KAWAKAMI; Kyoko TAJI; Ichiya NINOMIYA; Takeaki NAITO; Tadamasa DATE; Kimio OKAMURA

doi:10.1248/cpb.40.2579

Okiko MIYATA, Tetsuro SHINADA, Nanako KAWAKAMI, Kyoko TAJI, Ichiya NINOMIYA, Takeaki NAITO, Tadamasa DATE, Kimio OKAMURA

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Keywords: asymmetric synthesis, whisky lactone, cognac lactone, butyrolactone, nucleophilic addition, thiophenol, (+)-sultam, ate complex

JOURNAL FREE ACCESS

1992 Volume 40 Issue 9 Pages 2579-2581

DOI https://doi.org/10.1248/cpb.40.2579

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Abstract

A new stereoselective route to γ-butyrolactones such as (+)-trans-whisky and (+)-trans-cognac lactones (1a, b) has been developed by a combination of three key reactions : diastereoselective nucleophilic addition of thiophenol, cleavage of chiral N-acylsultam via thioester, and intramolecular displacement of the sulfonium group with carboxylate anion.

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