A Domino Diels–Alder Approach toward the Tetracyclic Nicandrenone Framework

A Domino Diels–Alder Approach toward the Tetracyclic Nicandrenone Framework

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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Bibliographic Details
Published in:Organic letters Vol. 17; no. 22; pp. 5517 - 5519
Main Authors: Mackay, Emily G, Nörret, Marck, Wong, Leon S.-M, Louis, Ignace, Lawrence, Andrew L, Willis, Anthony C, Sherburn, Michael S
Format: Journal Article
Language:English
Published: United States American Chemical Society 20-11-2015
Subjects:
Biological Products - chemistry
Furans - chemistry
Molecular Structure
Withanolides - chemistry
Online Access:Get full text
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Summary: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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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02412