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. 2005 Nov 16;127(45):15704-5.
doi: 10.1021/ja055041f.

Total synthesis of piericidin A1 and B1

Martin J Schnermann  1 , Dale L Boger
Affiliations

Total synthesis of piericidin A1 and B1

Martin J Schnermann et al. J Am Chem Soc. .

Abstract

The first total syntheses of piericidin A1 and B1 are disclosed and unambiguously establish the relative and absolute stereochemistry of the natural products by an approach that will facilitate the synthesis of a series of analogues. Central to the approach is an inverse electron demand Diels-Alder reaction of a N-sulfonyl-1-aza-1,3-butadiene with tetramethoxyethene followed by Lewis acid-promoted aromatization used to assemble the functionalized pyridine core. Additional key elements in the convergent approach include the use of an anti-aldol reaction to install the C9 and C10 relative and absolute stereochemistry, a modified Julia olefination for formation of the C5-C6 trans double bond with convergent assemblage of the side chain, and a penultimate heterobenzylic Stille cross-coupling reaction of the pyridyl core with the fully elaborated side chain.

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Figures

Scheme 1
Scheme 1
Synthesis of the Pyridine Core
Scheme 2
Scheme 2
Synthesis of 17
Scheme 3
Scheme 3
Synthesis of Piericidin A1 and B1
See this image and copyright information in PMC

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