Stereoselective synthesis of the tetrahydropyran core of polycarvernoside A.
[reaction: see text] A concise and stereoselective synthesis of the tetrasubstituted tetrahydropyran core of polycavernoside A was achieved in 55% overall yield from 3-benzyloxypropanal. A stereoselective allyl transfer reaction was used in the synthesis of enol ether 18 followed by a TFA-mediated cyclization to create the three new asymmetric centers in the tetrahydropyran with complete stereocontrol in a single-pot process.
Barry
Conor S
CS
School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
Bushby
Nick
N
Harding
John R
JR
Willis
Christine L
CL
D002384:Catalysis; D003500:Cyclization; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D000461:Rhodophyta / Q000737:chemistry; D013237:Stereoisomerism
D004187:Disaccharides; D018942:Macrolides; D011714:Pyrans; C121303:polycavernoside A