A Rapid, Asymmetric Synthesis of the Decahydrofluorene Core of the Hirsutellones
2009-02-05T00:00:00Z (GMT) by
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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