✦ LIBER ✦

Total synthesis of the piperidinol alkaloid (−)-(2R,3R,6S)-cassine

✍ Scribed by Jörg Oetting; Jens Holzkamp; Hartmut H. Meyer; Axel Pahl

Publisher: Elsevier Science
Year: 1997
Tongue: English
Weight: 480 KB
Volume: 8
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(96)00537-x

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✦ Synopsis

A highly efficient, flexible and diastereoselective route to all-cis-2,6disubstituted 3-piperidinols has been accomplished. The key component of the synthesis is a chiral I]-hydroxyester, which was obtained by iipase catalyzed kinetic resolution. Based on this starting material, diastereoselective alkylation of its dianion, Curtius rearrangement to a 2-oxazolidinone, Grignard reaction to introduce the side-chain and conversion of the aliphatic 2-oxazolidinone into a 3-piperidinol by imine cyclization lead to the exemplary total synthesis of naturally occurring (-)-(2R,3R,6S)-cassine.

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