Article ID Journal Published Year Pages File Type
5224393 Tetrahedron 2008 5 Pages PDF
Abstract

The C22-C34 fragment of antascomicin B lacking the C31 and C32 hydroxyl groups has been prepared in 11 steps from commercially available 2-hydroxy-cyclohexanone. An Ireland-Claisen rearrangement was employed to install the C26 and C27 stereocenters. Our recently reported diastereoselective acyclic 1,3-reductive transposition was used to establish the remote C23 stereocenter. Directed hydrogenation was employed to set the C29 stereocenter. The model compound contains five of the stereocenters and all of the carbons of the corresponding fragment of antascomicin B.

Graphical abstractDownload full-size image

Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
Authors
, ,