Total synthesis of the marine metabolite (-)-clavosolide D.
The first total synthesis of the marine natural product (-)-clavosolide D is described confirming the structure of the unsymmetrical 16-membered diolide glycosylated by permethylated d-xylose moieties. Following efficient assembly of the two tetrahydropyrans using stereoselective Prins cyclizations, the side chains were introduced via an allylation/isomerization/anti cyclopropanation sequence; the final macrolactonization step was achieved under Yamaguchi conditions.
Seden
Peter T
PT
School of Chemistry, University of Bristol, Cantock's Close, Bristol, U.K.
Charmant
Jonathan P H
JP
Willis
Christine L
CL
D000818:Animals; D003500:Cyclization; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D008958:Models, Molecular; D011161:Porifera
D018942:Macrolides; C470360:clavosolide D