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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 5
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Original Articles

A Facile Synthesis of Tetracycles of the γ-Lycorane Type

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Pages 381-386 | Received 11 Sep 1973, Published online: 05 Dec 2006
 

Abstract

When an attempted application of the general scheme of alkaloid synthesis, based on the partial hydrogenation of 1 -alkyl-3-acylpyridinium salts and acid-induced cyclization of the resultant 2-piperideines,2 to the construction of an Amaryllidaceae alkaloid system failed in the cyclization step, i.e. the transformation of dihydroisoquinoline 4a (prepared by the treatment of ester 2a 3 with 5-bromo-2 -pentanone ethylene ketal, followed by hydrogenation of the salt over palladium-charcoal) into a tricyclic ketal ester,4 an alternate, route of synthesis still utilizing a previously prepared isoquinoline precursor (3b) was investigated. The initial observation of the easy conversion of 3b into N-methyl (1a) and O-ethyl products (2b) was helpful in this connection.

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