Total synthesis of a diastereomer of the marine natural product clavosolide A.
The first total synthesis of the reported structure of the sponge metabolite clavosolide A is described using a Prins cyclisation to assemble the tetrahydropyran core followed by manipulation of the side-chain, dimerisation and finally glycosidation.
Barry
Conor S
CS
School of Chemistry, University of Bristol, Cantock's Close, Bristol, UK.
Bushby
Nick
N
Charmant
Jonathan P H
JP
Elsworth
Jon D
JD
Harding
John R
JR
Willis
Christine L
CL
D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D019281:Dimerization; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D009792:Oceans and Seas; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D018942:Macrolides; C455699:clavosolide A