A Domino Diels-Alder Approach toward the Tetracyclic Nicandrenone Framework

Emily G. MacKay; Marck Nörret; Leon S.M. Wong; Ignace Louis; Andrew L. Lawrence; Anthony C. Willis; Michael S. Sherburn

doi:10.1021/acs.orglett.5b02412

A Domino Diels-Alder Approach toward the Tetracyclic Nicandrenone Framework

Emily G. MacKay, Marck Nörret, Leon S.M. Wong, Ignace Louis, Andrew L. Lawrence, Anthony C. Willis, Michael S. Sherburn^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5517-5519
Number of pages	3
Journal	Organic Letters
Volume	17
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.5b02412
Publication status	Published - 20 Nov 2015

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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.",

author = "MacKay, {Emily G.} and Marck N{\"o}rret and Wong, {Leon S.M.} and Ignace Louis and Lawrence, {Andrew L.} and Willis, {Anthony C.} and Sherburn, {Michael S.}",

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AU - MacKay, Emily G.

AU - Nörret, Marck

AU - Wong, Leon S.M.

AU - Louis, Ignace

AU - Lawrence, Andrew L.

AU - Willis, Anthony C.

AU - Sherburn, Michael S.

PY - 2015/11/20

Y1 - 2015/11/20

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AB - 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.

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DO - 10.1021/acs.orglett.5b02412

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VL - 17

SP - 5517

EP - 5519

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

A Domino Diels-Alder Approach toward the Tetracyclic Nicandrenone Framework

Abstract

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