ol050840o_si_001.pdf (103.58 kB)
Stereoselective Synthesis of the Tetrahydropyran Core of Polycarvernoside A
journal contribution
posted on 2005-06-23, 00:00 authored by Conor S. Barry, Nick Bushby, John R. Harding, Christine L. WillisA 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.