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Paper | Regular issue | Vol 43, No. 7, 1996, pp.1497-1512
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7493
An Attempted Total Synthesis of Lysergic Acid via an Alkene/N-Sulfonylimine Cyclization

Janet L. Ralbovsky, Paul M. Scola, Eiichi Sugino, Carolina Burgos-Garcia, Steven M. Weinreb,* and Masood Parvez

*Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, U.S.A.

Abstract

Lewis acid-promoted cyclization of the N-tosylimine derived from aldehyde alkene (18) affords an interesting rearranged seven-membered ring tricycle (21) rather than the expected intermediate containing the lysergic acid skeleton.