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Synthetic Studies on Camptothecins. Part 1 : An Improved Asymmetric Total Synthesis of (20S)-Camptothecin

✍ Scribed by Li-Peng Zhang; Yong Bao; Yun-Yan Kuang; Fen-Er Chen

Publisher
John Wiley and Sons
Year
2008
Tongue
German
Weight
148 KB
Volume
91
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A six‐step asymmetric total synthesis of (20__S__)‐camptothecin (1) has been accomplished in 25% overall yield starting from the known pyridone 3. The key steps in this synthesis are the chemoselective Ni‐catalyzed hydrogenation of 3‐cyanopyridone 6 to 3‐formylpyridone 7 in AcOH/pyridine/H~2~O and the Davis asymmetric hydroxylation of tricyclic lactone 4 utilizing a chiral N‐sulfonyloxaziridine into (4′S)‐tricyclic hydroxylactone 2.

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