THE 1ST SYNTHESIS OF (+ -)-TAXODONE

Authors
SANCHEZ AJ KONOPELSKI JP
Citation
Aj. Sanchez et Jp. Konopelski, THE 1ST SYNTHESIS OF (+ -)-TAXODONE, Synlett, (5), 1994, pp. 335-336
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
5
Year of publication
1994
Pages
335 - 336
Database
ISI
SICI code
0936-5214(1994):5<335:T1SO(->2.0.ZU;2-G
Abstract
The total synthesis of (+/-)-taxodone (1) is described. The C-ring is formed by the cycloaddition of methyl acrylate with siloxy-furan 5 der ived from isodrimenin (4). The C13 isopropyl roup was introduced via a sulfur ylide rearrangement followed by reductive cleavage. Compound 1 was synthesized in 61% yield from diacetate 18 by deprotection and in tramolecular oxirane opening with potassium t-butoxide and water in TH F.