A model study for the total synthesis of (+/-)-scopadulin: stereoselective construction of the A/B ring system with desired functionalities

A model study toward the total synthesis of (+/-)-scopadulin is described. Stereocontrolled synthesis of the A/B ring system with desired functionalities was achieved by stereoselective cyanation of a bicyclic enone with Et2AlCN, diastereoselective construction of a quaternary carbon at C-4 with LDA...

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Bibliographic Details
Published inTetrahedron Vol. 57; no. 1; pp. 127 - 134
Main Authors Rahman, SMA, Ohno, H, Yoshino, H, Satoh, N, Tsukaguchi, M, Murakami, K, Iwata, C, Maezaki, N, Tanaka, T
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
STEMODANE DITERPENES
(+/-)-APHIDICOLIN
SCOPARIA-DULCIS L
APHIDICOLANE
diastereoselection
conjugate addition
deamination
copper and compounds
FORMAL TOTAL SYNTHESIS
ACID-B
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Summary:A model study toward the total synthesis of (+/-)-scopadulin is described. Stereocontrolled synthesis of the A/B ring system with desired functionalities was achieved by stereoselective cyanation of a bicyclic enone with Et2AlCN, diastereoselective construction of a quaternary carbon at C-4 with LDA-BOMCl, and conversion of the cyano group into a methyl group. (C) 2000 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/S0040-4020(00)00995-9