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Dedicated to Prof. Wilfred R. Chan for his inspiration and dedication to natural products chemistry. This paper describes the development of a highly stereoselective N-acyliminium cyclization protocol for the construction of a range of non-racemic heterocyclic templates. Due to the nature of this review, we have focused primarily on developments made within our own research group, but have included relevant and noteworthy contributions in the same area from others, most notably the research groups of Amat, Bosch and Lete. As a result, we apologize in advance for the omission of much excellent work carried out by many other talented researchers in this field.

We report a highly diastereoselective approach for the synthesis of the pentacyclic indole core of the manadomanzamine alkaloid skeleton, with complete control over the relative and absolute stereochemistries at the three contiguous stereocentres at ring positions 1, 10, and 24, from a readily available chiral template. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved

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