ORGN 292

Yonghai Chai, Zonghong Mou, T. David Bateman and Matthias C. McIntosh*. Department of Chemistry and Biochemistry, University of Arkansas, 115 Chemistry Bldg, Fayetteville, AR 72701

The massileunicellins are a small family of highly oxidized eunicellin diterpenes that possess a densely functionalized isobenzofuran core in which all eight of the ring carbons are stereocenters. In addition, they possess a tertiary alcohol stereocenter at C3 adjacent to the isobenzofuran. We have recently completed the synthesis of bicycle 3, possessing 7 of the 9 stereocenters of the natural product. Current efforts involve elaboration at C3 and closure of the oxonane ring. Details of the synthesis and further progress toward the target will be described.