Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5274854 | Tetrahedron Letters | 2008 | 4 Pages |
Abstract
The psymberin unsaturated 'psymberate' side chain 7 was synthesized in 7 steps (36% yield) with good diastereoselectivity using commercially available starting material to control the stereochemistry at C4 and C5. The synthesis of seco-psymberin was completed in an efficient manner based on a CuI mediated coupling reaction between vinyl iodide 8 and 'psymberamide' 7. In an attempt to synthesize natural psymberin from the seco-intermediate, a novel PhI(OAc)2 mediated cascade ring closing reaction was discovered. A possible mechanistic pathway for the formation of the ring closing product was presented.
Graphical abstractDownload full-size image
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Xianhai Huang, Ning Shao, Anandan Palani, Robert Aslanian, Alexei Buevich, Cynthia Seidel-Dugan, Robert Huryk,