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Totally Synthetic by Paul H. Docherty, 26 April 2006

Total Synthesis of Haouamine A


J. H. Jeong, S. M. Weinreb, Org. Lett. 2006, 8, 2309-2312.

DOI: 10.1021/ol060556c

Using some really smart 1,3-dipolar chemistry, Weinreb has completed a formal total synthesis of Haouamine. Working towards the Baran indenotetrahydropyridine pentacyclic intermediate, they used a 1,3-dipolar cycloaddition to install the indene system very quickly, but isolated two products from the cyclisation. However, the undesired product was converted to the desired by simply heating, resulting in a 76% yield.

However, the ambitious RCM chemistry using a terminal vinyl chloride was less successful, and required a rethinking to complete this work.