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Synthesis of (6 S ,7 S )‐7‐Hydroxy‐6,11‐cyclofarnes‐3(15)‐en‐2‐one, the Opposite Enantiomer of the Antibacterial Sesquiterpene from Premna oligotricha , and the ( R ) Enantiomer of Ancistrodial, the Defensive Sesquiterpene from Ancistrotermes cavithorax
Author(s) -
Horiuchi Sayo,
Takikawa Hirosato,
Mori Kenji
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199812)1998:12<2851::aid-ejoc2851>3.0.co;2-e
Subject(s) - sesquiterpene , chemistry , enantiomer , stereochemistry , absolute configuration , antibacterial activity , bacteria , genetics , biology
The absolute configuration of the antibacterial sesquiterpene, 7‐hydroxy‐6,11‐cyclofarnes‐3(15)‐en‐2‐one ( 2 ), was determined as (6 R ,7 R ) by the synthesis of its opposite enantiomer (6 S ,7 S )‐ 2 from ( S )‐2‐(2,2‐dimethyl‐6‐methylenecyclohexyl)ethanol ( 1 ). This versatile building block ( S )‐ 1 was also converted to ( R )‐ancistrodial ( 3 ).