A Domino Diels-Alder Approach toward the Tetracyclic Nicandrenone Framework

Mackay, Emily G; Nörret, Marck; Wong, Leon S-M; Louis, Ignace; Lawrence, Andrew L; Willis, Anthony C; Sherburn, Michael

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A Domino Diels-Alder Approach toward the Tetracyclic Nicandrenone Framework

Date

2015-11-20

Authors

Mackay, Emily G

Nörret, Marck

Wong, Leon S-M

Louis, Ignace

Lawrence, Andrew L

Willis, Anthony C

Sherburn, Michael

Abstract

The tetracarbocyclic framework of the nicandrenone natural products is formed in one step from a linear precursor via a domino intramolecular Diels-Alder/intramolecular furan Diels-Alder/aromatization sequence. The approach represents a new 0 → ABCD strategy for the preparation of aromatic steroids.