Chemical and pharmaceutical bulletin

Synthetic Studies on the Starfish Alkaloid Imbricatine. Construction of an ent-Imbricatine Framework.

M Ohba, M Imasho, T Fujii

Index: Ohba, Masashi; Imasho, Masaaki; Fujii, Tozo Chemical and Pharmaceutical Bulletin, 1999 , vol. 47, # 1 p. 83 - 89

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Citation Number: 4

Abstract

A chiral synthetic route to the amino esters 5 and 6, which contain the fundamental framework of ent-imbricatine (ent-3), has been developed as a prelude to the total synthesis of the starfish alkaloid imbricatine (3). The route started from the sulfur-containing L- phenylalanine derivative 7 and proceeded through key steps such as cyclization fo the amide 8 without racemization, reduction to the 1, 3-cis-tetrahydroisoquinoline 9, and ...