Total synthesis and configurational validation of (+)-phorbaside A.
The configurational assignment of the cytotoxic marine macrolide phorbaside A has been verified by the stereodefined synthesis of the proposed structure 1 and its (18S,19R)-diastereomer 3, followed by correlation using circular dichroism spectroscopy. This first total synthesis, which proceeds in 8.2% yield over 23 steps, features two 1,4-syn boron aldol reactions, a Sonogashira coupling, and an alpha-glycosylation to append the L-evalose sugar moiety.
Paterson
Ian
I
University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK.
Paquet
Tanya
T
D002942:Circular Dichroism; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D018942:Macrolides; C520582:phorbaside A