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Total synthesis of the antimitotic marine macrolide (-)-leiodermatolide.

Angewandte Chemie (International ed. in English) (2014-02-01)
Ian Paterson, Kenneth K-H Ng, Simon Williams, David C Millican, Stephen M Dalby
ABSTRACT

Leiodermatolide is an antimitotic macrolide isolated from the marine sponge Leiodermatium sp. whose potentially novel tubulin-targeting mechanism of action makes it an exciting lead for anticancer drug discovery. In pursuit of a sustainable supply, we report a highly stereocontrolled total synthesis (3.2% yield) based on a convergent sequence of palladium-mediated fragment assembly and macrolactonization. Boron-mediated aldol reactions were used to configure the three key fragments 2, 5, and 6 by employing the appropriate enantiomer of the lactate-derived ketone 7.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1-(Trimethylsilyl)imidazole, 96%
Sigma-Aldrich
N-(5-Chloro-2-pyridyl)bis(trifluoromethanesulfonimide), 96%
Sigma-Aldrich
Trichloroacetyl isocyanate, purum, ≥97.0% (GC)

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