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

25 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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10.1021/acs.orglett.5b02412

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title = "A Domino Diels-Alder Approach toward the Tetracyclic Nicandrenone Framework",

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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doi = "10.1021/acs.orglett.5b02412",

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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.

UR - https://www.scopus.com/pages/publications/84948141396

U2 - 10.1021/acs.orglett.5b02412

DO - 10.1021/acs.orglett.5b02412

M3 - Article

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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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