Synthesis of (+)-didemniserinolipid B via ketalization/ring-closing metathesis.
A modular synthesis of didemniserinolipid B is reported. Central to this synthesis was the use of a ketalization/ring-closing metathesis (K/RCM) strategy to establish the 6,8-dioxabicyclo[3.2.1]octane core. The C10 axial alcohol was established via a selective epoxidation, followed by reductive trans-diaxial epoxide opening. The serinol and unsaturated ester side chains were introduced by a Williamson etherification and cross metathesis, respectively.
Marvin
Christopher C
CC
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1322, USA.
Voight
Eric A
EA
Burke
Steven D
SD
D003500:Cyclization; D004987:Ethers / Q000737:chemistry; D011409:Propylene Glycols / Q000138:chemical synthesis*
D004987:Ethers; D011409:Propylene Glycols; C467921:didemniserinolipid B