Journal of Organic Chemistry p. 773 - 784 (1986)
Update date:2022-09-26
Topics:
Bosch, M. Pilar
Camps, Francisco
Coll, Jose
Guerrero, Angel
Tatsuoka, Toshio
Meinwald, Jerrold
A stereoselective 14-step, total synthesis of (+/-)-muzigadial (1a, 11percent overall yield), starting from the commercially available Wieland-Miescher ketone (5), via intermediate ketone 13, is described.The two additional chiral centers in 13 were incorporated by equilibrium of the mixture of stereoisomeric ketones 10 to the most favorable isomer, 10a.The key step for introducing the necessary functionality at C-1 involved the regio- and stereoselective cis hydroxylation of enol ether 37b with osmium tetraoxide in the presence of tert-butyl hydroperoxide.
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