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A rapid, asymmetric synthesis of the decahydrofluorene core of the hirsutellones.

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.

SUBMITTER: Tilley SD

PROVIDER: S-EPMC3115586 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

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A rapid, asymmetric synthesis of the decahydrofluorene core of the hirsutellones.

Tilley S David SD Reber Keith P KP Sorensen Erik J EJ

Organic letters 20090201 3

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 thi ...[more]

PMID: 19119873

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