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A rapid, asymmetric synthesis of the Decahydrofluorene core of the hirsutellones


Tilley, S David; Reber, Keith P; Sorensen, Erik J (2009). A rapid, asymmetric synthesis of the Decahydrofluorene core of the hirsutellones. Organic Letters, 11(3):701-703.

Abstract

A tandem ketene-trapping/Diels-Alder cyclization sequence was the pivotal transformation in an efficient, asymmetric synthesis of a decahydrofluorene tricyclic structure possessing eight stereogenic centers and key features of the hirsutellone class of antitubercular natural products. The hirsutellone-like beta-keto ester that was fashioned by this sequence (13 steps; 6% overall yield) demonstrated significant inhibitory activity against Mycobacterium tuberculosis. The mechanism of action of this antitubercular compound is not yet known.

A tandem ketene-trapping/Diels-Alder cyclization sequence was the pivotal transformation in an efficient, asymmetric synthesis of a decahydrofluorene tricyclic structure possessing eight stereogenic centers and key features of the hirsutellone class of antitubercular natural products. The hirsutellone-like beta-keto ester that was fashioned by this sequence (13 steps; 6% overall yield) demonstrated significant inhibitory activity against Mycobacterium tuberculosis. The mechanism of action of this antitubercular compound is not yet known.

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34 citations in Web of Science®
17 citations in Scopus®
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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2009
Deposited On:27 May 2015 15:38
Last Modified:05 Apr 2016 19:15
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
Free access at:PubMed ID. An embargo period may apply.
Publisher DOI:https://doi.org/10.1021/ol802768p
PubMed ID:19119873

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