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.