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Studies in marine polypropionate synthesis: total synthesis of (-)-baconipyrone C
I Paterson1, D Y Chen, J L Aceña
1University Chemical Laboratory, Lensfield Road, Cambridge, UK. ip100@cus.cam.ac.uk
Organic Letters
|June 7, 2000
Abstract:
[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.