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A Concise Synthesis of ( E )‐ and ( Z )‐Neomanoalides
Author(s) -
Jefford Charles W.,
Rossier JeanClaude,
Boukouvalas John,
Huang Pingzhong
Publication year - 1994
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19940770309
Subject(s) - chemistry , bromide , reagent , hydrolysis , furan , medicinal chemistry , stereochemistry , organic chemistry
The first synthesis of ( Z )‐neomanoalide ( 4 ) and an improved synthesis of its ( E )‐isomer 3 was accomplished in a concise, regiocontrolled manner by exploiting 2‐[( tert ‐butyl)dimethylsiloxy]‐4{[( tert ‐butyl)dimethylsiloxy]‐methyl}furan ( 6 ) as the key reagent. Lithiation of 6 and subsequent reaction with the (2 Z )‐ or (2 E )‐isomer of (6 E )‐3‐{[( tert ‐butyl)dimethylsiloxy]methyl}‐7‐methyl‐9‐(2′,6′,6′‐trimethylcyclohex‐1′‐enyl)nona‐2,6‐dienyl bromide ( 5 ), followed by hydrolysis, afforded the corresponding neomanoalide.