✦ LIBER ✦

Total synthesis of (±) podophyllotoxin

✍ Scribed by T Kaneko; H Wong

Book ID: 104227413
Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 166 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)95770-8

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✦ Synopsis

A straightforward approach to podophyllotoxin was developed using silyl enol ether 5.

Podophyllotoxin (1) is a lignan isolated from Podophyllum peltatum and p. ml.

It is a potent inhibitor of microtubule assembly and a key intermediate of an antitumor agent, etoposide (2)'. Although there have been several elegant syntheses of this compound or its C4 epimer (epipodophyllotoxin)3, we sought an operationally simpler route, which is the subject of this letter.

The challenge of the synthesis lies in the formation of four contiguous stereocenters and the presence of a base-sensitive trans lactone. Two of the published

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