Specific C−C Bond Construction by Remote C−H Activation:  Synthesis of (−)-<i>trans</i>-Cembranolide

1997-09-19T00:00:00Z (GMT) by Douglass F. Taber Ying Song
The first total synthesis of (−)-<i>trans</i>-cembranolide (<b>1</b>), isolated from <i>Sinularia mayi</i> Luttschw., is described. The key step in the synthesis is the diastereoselective Rh-mediated cyclization of the enantiomerically pure diazo ester <b>4</b> to the tetrahydrofuran <b>3a</b>.