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A Rapid, Asymmetric Synthesis of the Decahydrofluorene Core of the Hirsutellones.

  作者 Tilley, S. David;Reber, Keith P.;Sorensen, Erik J.;  
  选自 期刊  Organic Letters;  卷期  2009年11-3;  页码  701-703  
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[摘要]A tandem ketene-trapping/Diels-Alder cyclization sequence was the pivotal transformation in an efficient, asym. synthesis of a decahydrofluorene tricyclic structure I possessing eight stereogenic centers and key features of the hirsutellone class of antitubercular natural products. The hirsutellone-like b-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 compd. is not yet known.

 
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