Stereloselective synthesis of the tetrahydropyran core of polycarvernoside A

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...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 7; no. 13; pp. 2683 - 2686
Main Authors Barry, CS, Bushby, N, Harding, Willis, CL
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 23.06.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIHYDROPYRANS
ETHERS
ACID
COPE REARRANGEMENTS
PRINS-TYPE CYCLIZATION
HOMOALLYLIC ALCOHOLS
ALDEHYDES
STEREOSELECTIVE-SYNTHESIS
ALLYL-TRANSFER REACTION
STEREOCONTROLLED SYNTHESIS
Online AccessGet full text

Cover

More Information
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol050840o