Model studies related to CP-225,917: Stereocontrolled generation of the quaternary center

Citation
Dlj. Clive et Jh. Zhang, Model studies related to CP-225,917: Stereocontrolled generation of the quaternary center, TETRAHEDRON, 55(41), 1999, pp. 12059-12068
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
41
Year of publication
1999
Pages
12059 - 12068
Database
ISI
SICI code
0040-4020(19991008)55:41<12059:MSRTCS>2.0.ZU;2-F
Abstract
The enolate derived from ester 15 reacts with diketone 10 stereoselectively (10:1), and the major isomer can be converted into lactone 21. This rearra nges in boiling 1,2-dichlorobenzene to afford the tricyclic lactone 22, a m odel compound which shares with CP-225,917 (1) the bridgehead double bond, the C(5) quaternary center, a C(5) side chain of correct length, and the ga mma-lactone subunit. (C) 1999 Elsevier Science Ltd. All rights reserved.