Studies directed toward the synthesis of the massileunicellins

by Chai, Yonghai; McIntosh, Matt C.

An approach to the massileunicellins is described that employs a cycloaldol reaction to assemble the isobenzofuran bicyclic core. A stereoselective rearrangement-epoxidation-oxidation cascade and a chelation controlled addition to a hindered acyl furan are used to install the C3, C11, C12, and C13 oxygens. The synthesis establishes eight of the nine stereocenters present in the isobenzofuran core of the massileunicellins. (C) 2004 Published by Elsevier Ltd.

Journal
Tetrahedron Letters
Volume
45
Issue
16
Year
2004
Start Page
3269
ISBN/ISSN
1873-3581; 0040-4039
DOI
10.1016/j.tetlet.2004.02.112