Asymmetric synthesis of (+)-passifloricin A and its 6-epimer

Stereoselective total syntheses of the antiprotozoal natural product (+)-passifloricin A and its C-6 epimer have been achieved in ∼5% overall yield. The strategy is based on Jacobsen epoxidation, Grubbs’ metathesis and an Evans’ intramolecular oxa-Michael reaction.

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2008-07, Vol.49 (29), p.4476-4478
Main Authors: Chandrasekhar, S., Rambabu, Ch, Reddy, A. Syamprasad
Format: Article
Language:English
Subjects:
Evans’ intramolecular oxa-Michael reaction
Grubbs’ metathesis
Jacobsen epoxidation
Maruoka allylation
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Stereoselective total syntheses of the antiprotozoal natural product (+)-passifloricin A and its C-6 epimer have been achieved in ∼5% overall yield. The strategy is based on Jacobsen epoxidation, Grubbs’ metathesis and an Evans’ intramolecular oxa-Michael reaction.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.05.070