Bulletin of the Chemical Society of Japan, volume 50, issue 6, pages 1575-1579

A Convenient Synthesis of (±)-Taxodione, (±)-Ferruginol, and (±)-Sugiol

TAKASHI MATSUMOTO
SHUJI USUI
Toshitaka Morimoto
Publication typeJournal Article
Publication date1977-06-01
scimago Q2
wos Q2
SJR0.665
CiteScore6.4
Impact factor3.3
ISSN00092673, 13480634
General Chemistry
Abstract
The condensation of β-cyclocitral (4); with 3-isopropyl-4-methoxybenzyl chloride (5) in the presence of lithium naphthalenide gave an alcohol (6), which was then oxidized to the corresponding α,β-unsaturated ketone (7). The Intramolecular cyclization of 7 with polyphosphoric acid yielded (±)-12-methoxyabieta-8,11,13-trien-6-one (8) and its cis-isomer (9), which was then successfully converted into 8 via an enol acetate (11). The 8 ketone was dem ethylated with boron tribromide to give a phenol (18), and this was then reduced with lithium aluminium hydride to yield the corresponding alcohol (19). The oxidation of the C-11 position in 19 with benzoyl peroxide gave (±)-12-benzoyloxyabieta-8,11,13-trien-6β,11-diol (20), which, on reduction with lithium aluminium hydride and subsequent oxidation with Jones reagent, afforded (±)-taxodione (1). The reductive cleavage of the hydroxyl group in 6 with dichloroaluminium hydride, followed by cyclization, gave (±)-ferruginyl methyl ether (12), which was then demethyla...

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