A Chiral Auxiliary-based Synthesis Of The C5–C17 Trans-decalin ...

A chiral auxiliary-based synthesis of the C5–C17 trans-decalin framework of anthracimycin†

Jared L. Freeman, ab Margaret A. Brimble *ab and Daniel P. Furkert *ab Author affiliations

* Corresponding authors

a School of Chemical Sciences, The University of Auckland, Symonds Street, Auckland 1010, New Zealand E-mail: [email protected], [email protected]

b Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, Symonds Street, Auckland 1010, New Zealand

Abstract

Synthetic studies towards the potent antimicrobial natural product anthracimycin, including the successful synthesis of the trans-decalin fragment through an endo-selective intramolecular Diels–Alder reaction are reported. The synthesis utilised a highly E-selective Julia–Kocienski olefination to access a stable skipped triene intermediate which provided access to four cycloaddition precursors for comprehensive Diels–Alder investigation. Incorporation of a chiral Evans’ oxazolidinone auxiliary overrode the inherent facial selectivity of the Diels–Alder reaction. These synthetic studies provide a platform for further investigation of this natural product as a novel chemical scaffold for antimicrobial drug discovery.

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