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

School of Chemistry

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

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
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

http://pubs.acs.org/doi/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.}",

year = "2015",

month = nov,

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

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journal = "Organic letters",

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T1 - A Domino Diels–Alder Approach toward the Tetracyclic Nicandrenone Framework

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

N2 - 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.

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.

U2 - 10.1021/acs.orglett.5b02412

DO - 10.1021/acs.orglett.5b02412

M3 - Article

VL - 17

SP - 5517

EP - 5519

JO - Organic letters

JF - Organic letters

SN - 1523-7060

IS - 22

ER -

A Domino Diels–Alder Approach toward the Tetracyclic Nicandrenone Framework

Abstract

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