✦ LIBER ✦
Syntheses of (+)-(S,S)-(cis-6-Methyltetrahydropyran-2-yl)acetic acid and of (−)-(R,R)-Didesoxy-pyrenophorine Using a New d5-Reagent. Preliminary communication
✍ Scribed by Dieter Seebach; Manat Phmakotr
- Publisher
- John Wiley and Sons
- Year
- 1979
- Tongue
- German
- Weight
- 241 KB
- Volume
- 62
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
The Li/K‐derivative 6 is used to synthesize the title compounds (3a and 4a) in enantiomerically pure form from (−)‐(S)‐propylene epoxide. The C,C bond forming key step leading to the hydroxyketone 7 is followed by cyclization (→, 8), Beckmann cleavage (→ 9b) and hydrolysis to 3a (recently isolated from civet). Base treatment of 3a opens the ring (10) to give the hydroxyacid 1 which is cyclized to the macrolide 4a. The synthetic usefulness of the highly nucleophilic doubly reduced dienone system 6 as d^5^‐reagent (see synthons 2) is thus demonstirated.