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Note | Special issue | Vol 74, No. 1, 2007, pp.943-950
Published online, 28th August, 2007
DOI: 10.3987/COM-07-S(W)14
A Novel Reductive Amino-Cyclization Method and Its Application for the Total Syntheses of (±)-Aurantioclavine and (±)-Lophocerine

Masanori Somei* and Fumio Yamada

*Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan

Abstract

A novel reductive amino-cyclization method for the synthesis of azacycloalkanes is developed. Its versatility is proved by the total syntheses of (±)-aurantioclavine (1), an ergot alkaloid, and (±)-lophocerine (2), a cactus alkaloid, as examples of azepane and piperidine skeletons, respectively.