Asymmetric total synthesis of (+)-milbemycin D

…, IM Vallin, WG Hollis, R O'Mahony…

Index: Crimmins, Michael T.; Al-awar, Rima S.; Vallin, Isabelle M.; Hollis Jr., W. Gary; O'Mahony, Rosemary; Lever, John G.; Bankaitis-Davis, Danute M. Journal of the American Chemical Society, 1996 , vol. 118, # 32 p. 7513 - 7528

Full Text: HTML

Citation Number: 39

Abstract

The enantioselective total synthesis of the potent antiparasitic agent milbemycin D (1) has been achieved. The spiroketal fragment is prepared through a novel spiroketalization of a hydroxy pyrone to set the anomeric stereocenter and establish functionality for the stereocontrolled attachment and subsequent extension of the connecting chain between the spiroketal and the hexahydrobenzofuran fragment. The hexahydrobenzofuran fragment is ...