Concise total synthesis of (-)-muricatacin by tandem ring-closing/cross metathesis.
A strategy for the synthesis of chiral 5-(1-hydroxyalk-2-enyl)-5H-furan-2-ones and its application to the total synthesis of (-)-muricatacin, in four steps and 37% overall yield from (R,R)-hexa-1,5-diene-3,4-diol, are described. The key synthetic step in this approach is a highly regioselective and stereoselective tandem ring-closing/cross metathesis reaction in which both lactone formation and alkyl chain extension are accomplished in an efficient one-pot process.
Quinn
Kevin J
KJ
Department of Chemistry, College of the Holy Cross, Worcester, Massachusetts 01610-2395, USA. kquinn@holycross.edu
Isaacs
André K
AK
Arvary
Rebecca A
RA
D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy
D005663:Furans; C082488:muricatacin