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
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.