| Abstract
| - The side chain of the insecticidal steroid petuniasterone D was synthesized by the biomimetic acid-catalyzed epoxy ester−ortho ester rearrangement. In addition to the natural (22R,24R)-configurationof the side chain ortho ester, compounds bearing the epimeric (22R,24S)-, (22S,24R)-, and (22S,24S)- [3.2.1]-bicyclic ortho esters were also produced by stereospecific rearrangement of thecorresponding isomeric epoxy esters. Functionalization of the steroid nucleus of the (22R,24R)-ortho ester completed the synthesis of the natural product.
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