First stereoselective synthesis of (1S,2S,4R,5R)-(−)-β-multistriatin
✍ Scribed by Henrichfreise, Peter ;Scharf, Hans-Dieter
- Publisher
- John Wiley and Sons
- Year
- 1995
- Tongue
- English
- Weight
- 510 KB
- Volume
- 1995
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
Starting from 2,3‐O‐(3‐pentylidene)‐D‐glyceraldehyde (3), we prepared the bicyclic pheromone (1__S__,2__S__,4__R__,5__R__)‐(−)‐β‐multistriatin (1) on a gram scale. Key steps of the synthesis are a cis‐selective Wittig olefination followed by diastereo‐selective Michael addition and hydrogenation.
📜 SIMILAR VOLUMES
## Abstract A convenient preparation of (1__R__,2__S__,3__R__,4__S__)‐3‐(neopentyloxy)isoborneol (= (1__R__,2__S__,3__R__,4__S__)‐3‐(2,2‐dimethyl‐propoxy)‐1,7,7‐trimethylbicyclo[2.2.1]heptan‐2‐ol; 1a), a valuable chiral auxiliary, is described. The synthesis involves six steps starting from the rea
The condensation of (1 R,2S) or (lS,2S)-N,N'-dimethyI-l-phenylpropane-l 2-diamines with aldehydes gives respectively two diastereorneric 2-alkyl-l,3,4-trimethyI-S-phen limidazolidines. At thermodynamical equilibrium the major isomer in the erythro series is this one where t f ! e substituents at pos