Studies in marine polypropionate synthesis: total synthesis of (-)-baconipyrone C.
[reaction--see text] An asymmetric total synthesis of the unusual siphonariid metabolite, (-)-baconipyrone C (3), is described. Key steps included a tin(II)-mediated aldol coupling for the preparation of the carboxylic acid 17 and two different boron-mediated aldol additions leading to alcohol 8. Ester formation using modified Yamaguchi conditions gave 24, leading on PMB deprotection to (-)-baconipyrone C.
Paterson
I
I
University Chemical Laboratory, Lensfield Road, Cambridge, UK. ip100@cus.cam.ac.uk
Chen
D Y
DY
Aceña
J L
JL
Franklin
A S
AS
D000818:Animals; D001685:Biological Factors / Q000138:chemical synthesis / Q000737:chemistry; D008386:Marine Biology; D008974:Mollusca / Q000737:chemistry*; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D011422:Propionates / Q000138:chemical synthesis / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry
D001685:Biological Factors; D011108:Polymers; D011422:Propionates; D011753:Pyrones; C410203:baconipyrone C