PHENOL BENZYLIC EPOXIDE TO QUINONE METHIDE ELECTRON REORGANIZATION - SYNTHESIS OF (+ -)-TAXODONE/

Authors
SANCHEZ AJ KONOPELSKI JP
Citation
Aj. Sanchez et Jp. Konopelski, PHENOL BENZYLIC EPOXIDE TO QUINONE METHIDE ELECTRON REORGANIZATION - SYNTHESIS OF (+ -)-TAXODONE/, Journal of organic chemistry, 59(18), 1994, pp. 5445-5452
Citations number
82
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
18
Year of publication
1994
Pages
5445 - 5452
Database
ISI
SICI code
0022-3263(1994)59:18<5445:PBETQM>2.0.ZU;2-8
Abstract
The total synthesis of(+/-)-taxodone (1) is described. The C-ring is f ormed by the cycloaddition of methyl acrylate with furan 8, the latter derived from isodrimenin. The C13 isopropyl group was introduced via a sulfur ylide rearrangement followed by reductive cleavage. Compound I was synthesized in 61% yield by deprotection and intramolecular oxir ane opening of diacetate 31 with potassium tert-butoxide and water in THF.