The controlled degradation of avermectin B1a

✍ Scribed by Stephen Hanessian; Antonio Ugolini; Paul J Hodges; Daniel Dubé

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 246 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)84620-1

✦ Synopsis

gummary -An efficient oxidative degradation of avermectin Bla affording suitably functionalized Cl-C10 and Cll-Czs segments is reported.

Recently, we reported a stereospecific total synthesis' of the Cll-C2s segment of the potent anthelmintic agent (+I-avermectin Bla,' culminating in the synthesis of the natural product in enantiomerically pure form.3 In conjunction with these studies, we have developed an efficient degradation of the natural product, 4 in order to obtain suitably functionalized segments of avermectin Bla, that might be used to confirm the structures of intermediates obtained via synthesis, and to utilize them as precursors to hybrid or semi-synthetic analogs. s-SchemeI