Randall S. Matthews

Studies in the Total Synthesis of Mono- and Sesquiterpenes. Antirride

Abstract Pursuant to our investigations into the use of bicyclo[3.3.0]-octane derivatives in synthesizing cyclopentanoid monoterpenes,1 we were prompted to develop an efficient route to a synthetic equivalent of 1, an attractive entry to such natural products as morroniside,2 loganin,3 plumericin,4 and sarracenin.5 The target chosen was compound 2, an established derivative of the natural product antirride,6 characterized in 1969, but unknown synthetically. We now wish to report the synthesis of 2, as a prelude to the synthetic studies of plumericin4 and sarracenin5.

Total synthesis and X-ray crystal structure of 13,14-didehydro-11-deoxy-11-methyl-l5-oxoprostaglandin E1

A new 11-methylated prostaglandin analogue bearing the unusual 13,14-didehydro-15-oxo bottom side-chain has been prepared by total synthesis. Its complete structure has been established unambiguously by a single crystal X-ray analysis.