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First stereoselective synthesis of (1 S ,2 S ,4 R ,5 R )‐(−)‐β‐multistriatin
Author(s) -
Henrichfreise Peter,
Scharf HansDieter
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199506143
Subject(s) - stereoselectivity , chemistry , wittig reaction , stereochemistry , bicyclic molecule , key (lock) , gram , organic chemistry , catalysis , bacteria , computer science , biology , genetics , computer security
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.