Diisobutylaluminum Hydride Reduction of Unsaturated Sylylcyanohydrins: A New Entry to Confertifolin
- 1 August 1989
- journal article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 19 (13-14) , 2467-2480
- https://doi.org/10.1080/00397918908052649
Abstract
A new entry to the drimane-related sesquiterpene Confertifolin is reported. The key step involves the conversion of a β-phenylthio-α, β-unsaturated ketone into the corresponding silylcyanohydrin followed by diisobutylaluminum hydride reduction to the homologous α,β-unsaturated aldehyde.Keywords
This publication has 16 references indexed in Scilit:
- Reactions of .alpha.-oxo ketene dithioacetals with dimethylsulfonium methylide: a new versatile synthesis of furans and butenolidesThe Journal of Organic Chemistry, 1984
- A new approach for the regiospecific annelation of butenolidesThe Journal of Organic Chemistry, 1984
- Synthesis of the drimane-related sesquiterpenes euryfuran, confertifolin, and valdiviolideJournal of the Chemical Society, Perkin Transactions 1, 1983
- Total synthesis of (.+-.)-triptonide and (.+-.)-triptolideJournal of the American Chemical Society, 1982
- A new simple synthesis of variously substituted furans and butenolidesJournal of the Chemical Society, Chemical Communications, 1982
- Ozonolysis of phenolic dehydroabietane derivatives. Syntheses of optically active (+)-confertifolin, (+)-valdiviolide, (+)-winterin, (+)-isodrimenin, and (+)-pallescensin A.CHEMICAL & PHARMACEUTICAL BULLETIN, 1981
- Convenient syntheses of 5,5,9-trimethyl-trans-1-decalone and 6.beta.-hydroxy-5,5,9.beta.-trimethyl-trans-1-decaloneThe Journal of Organic Chemistry, 1979
- New selective carbonyl blocking group. Regioselective protection of p-quinonesJournal of the American Chemical Society, 1973
- Stereoselective method for the synthesis of both olefinic isomers from a single precursor. Conjugate reduction of .alpha.,.beta.-unsaturated epoxidesJournal of the American Chemical Society, 1973
- Cyanosilylation of aldehydes and ketones. A convenient route to cyanohydrin derivativesJournal of the Chemical Society, Chemical Communications, 1973