Synthetic Approach for (+)-Africanol
- 1 December 1990
- journal article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 19 (12) , 2295-2298
- https://doi.org/10.1246/cl.1990.2295
Abstract
Syntheses of (+)-africanol (1) and (+)-isoafricanol (2) were attempted by reductive radical cyclization of (1S,2S,8S)-2-(4′-butenyl)-1,5,5-trimethyl-bicyclo[5.1.0]-3-octanone derived from (1R,2S,4S,8S)-4-alkoxy-1,6,6-trimethyl-tricyclo[6.1.0.O2,4]nonane. This cyclization gave (+)-1 and (+)-2 as minor components, together with trans fused epimers as major components.This publication has 12 references indexed in Scilit:
- Diastereo-differentiating simmons-smith reaction using 2,4-pentanediol as a chiral auxiliaryTetrahedron Letters, 1988
- Total synthesis of the marine sesquiterpenes dactylol and africanol. De novo construction of a cyclooctanoid natural product from cycloheptane precursorsJournal of the American Chemical Society, 1987
- Total synthesis of africanolTetrahedron Letters, 1986
- New trans-fused africanols from leptographium lundbergiiTetrahedron, 1986
- Conformationally selective transannular cyclizations of humulene 9,10-epoxide. Synthesis of the two skeletally different cyclohumulanoids: dl-bicyclohumulenone and dl-africanolTetrahedron Letters, 1980
- Chemistry of organosilicon compounds. 99. Conjugate addition of allylsilanes to .alpha.,.beta.-enones. A New method of stereoselective introduction of the angular allyl group in fused cyclic .alpha.,.beta.-enonesJournal of the American Chemical Society, 1977
- Measurements of Bijvoet differences. Structure and absolute configuration of africanol, a sesquiterpeneActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1976
- New reagents for the intermolecular and intramolecular pinacolic coupling of ketones and aldehydesThe Journal of Organic Chemistry, 1976
- Reactions involving electron transfer. II. Reductions of enones with alkali metal solutionsJournal of the American Chemical Society, 1970
- Eine neue Synthese von Aziridinen durch Reduktion von α-Chlornitrilen mit LithiumaluminiumhydridBulletin of the Chemical Society of Japan, 1967