Synthesis of thromboxane B2 via ketalization/ring-closing metathesis.
Total synthesis of thromboxane B2 using intermolecular ketalization followed by ring-closing metathesis is reported. Other key steps include a Sharpless asymmetric epoxidation to form an oxirane on the endo face of the bicyclic acetal, epoxide opening using lithioacetonitrile, an allylic alcohol 1,3-transposition, and Mitsunobu lactonization.
Marvin
Christopher C
CC
Department of Chemistry, University of Wisconsin--Madison, 1101 University Avenue, Madison, Wisconsin 53706-1322, USA.
Clemens
Alexander J L
AJ
Burke
Steven D
SD
D003500:Cyclization; D013929:Thromboxane B2 / Q000138:chemical synthesis*
D013929:Thromboxane B2