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Haouamine A   

26 April 2006 6,730 views 6 Comments

Haouamine A.jpg

Weinreb and Jeong. Org. Let., 2006, ASAP. DOI: 10.1021/ol060556c

Using some really smart 1,3-di-polar chemistry, Weinreb has completed a formal synthesis of Haouamine. Working towards the Baran indenotetrahydropyridine pentacyclic intermediate, they used a 1,3-DPC to put in 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.

Haouamine A_2.jpg

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

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  • NoName says:

    for ambitious RCM, one might try ‘relay-RCM’. synthetic pathway seems to be flexble enough to incorporate ‘necessary tethers’.

  • ? says:

    So how does the weinreb route compare to the baren? Quicker?

  • Tot. Syn. says:

    Phil Baren’s route is far quicker on paper, consisting of only five steps, but most of the precursors aren’t commercial, so it starts adding up to more than that. However, his route is very neat.

  • […] JACS. It was followed up by an Angewandte two years later, but I’ve apparently only covered Weinreb’s synthesis, also back in 2006.  Part of the reason for all this interest is that the molecule seems to […]

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