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

Authors
Rahman, SMA Ohno, H Yoshino, H Satoh, N Tsukaguchi, M Murakami, K Iwata, C Maezaki, N Tanaka, T
Citation
Sma. Rahman et al., A model study for the total synthesis of (+/-)-scopadulin: stereoselectiveconstruction of the A/B ring system with desired functionalities, TETRAHEDRON, 57(1), 2001, pp. 127-134
Citations number
27
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
1
Year of publication
2001
Pages
127 - 134
Database
ISI
SICI code
0040-4020(20010101)57:1<127:AMSFTT>2.0.ZU;2-Q
Abstract
A model study toward the total synthesis of (+/-)-scopadulin is described. Stereocontrolled synthesis of the A/B ring system with desired functionalit ies was achieved by stereoselective cyanation of a bicyclic enone with Et2A lCN, diastereoselective construction of a quaternary carbon at C-4 with LDA -BOMCl, and conversion of the cyano group into a methyl group. (C) 2000 Els evier Science Ltd. All rights reserved.