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Communication | Special issue | Vol 79, No. 1, 2009, pp.373-378
Published online, 16th January, 2009
DOI: 10.3987/COM-08-S(D)42
Synthetic Studies toward (+)-Lysergic Acid: Construction of the Tetracyclic Ergoline Skeleton

Tohru Inoue, Satoshi Yokoshima, and Tohru Fukuyama*

*Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Abstract

We have successfully constructed the tetracyclic skeleton of lysergic acid, which features an acylation at the C3 position of the indole as well as an intramolecular Heck reaction. The optically active D ring unit could be derived from L-pyroglutamic acid via a disrotatory electrocyclic reaction of a dibromocyclopropane.