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

S. David Tilley; Keith P. Reber; Erik J. Sorensen

doi:10.1021/ol802768p

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

S. David Tilley, Keith P. Reber, Erik J. Sorensen

Chemistry

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

47 Scopus citations

Abstract

(Chemical Equation Presented) 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 β-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.

Original language	English (US)
Pages (from-to)	701-703
Number of pages	3
Journal	Organic letters
Volume	11
Issue number	3
DOIs	https://doi.org/10.1021/ol802768p
State	Published - Feb 5 2009

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol802768p

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abstract = "(Chemical Equation Presented) 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 β-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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AU - Reber, Keith P.

AU - Sorensen, Erik J.

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N2 - (Chemical Equation Presented) 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 β-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.

AB - (Chemical Equation Presented) 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 β-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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A rapid, asymmetric synthesis of the decahydrofluorene core of the hirsutellones

Abstract

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