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Communication | Regular issue | Vol 45, No. 7, 1997, pp.1263-1266
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7821
Simple Total Syntheses of (-)-Ergot Alkaloids and Thier (+)-Enantiomers by a Common Synthesis Method Utilizing Optical Resolution

Masanori Somei* and Kyoko Nakagawa

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan

Abstract

The first and simple total syntheses of (-)-isochanoclavine-I ((-)-1b), (-)-agroclavine ((-)-3), (-)-agroclavine-I ((-)-4), and (-)-norchanoclavine-I ((-)-5c) and their (+)-enantiomers are achieved from indole-3-carboxaldehyde (8) by a common synthesis method utilizing optical resolution. Absolute configuration of (-)-agroclavine-I is determined to be 5R and 10S for the first time. Preparations of both enantiomers of chanoclavine-I (1c) are also included.