Synthetic studies on spinosyn A. Convenient enantioselective construction of a suitably functionalized trans,anti,cis-decahydro-as-indacene intermediate via [3.3] sigmatropy and double configurational inversion

✍ Scribed by Leo A. Paquette; Zhongli Gao; Zhijie Ni; Graham F. Smith

• Book ID: 104256442
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 184 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00069-5

✦ Synopsis

An enantioselective route to the decahydro-as-indacene 15 is described. Anionic oxy-Cope rearrangement of alcohol 5 initiates the sequence, which capitalizes on thermodynamics to control ultimate elaboration of the four key stereogenic centers resident in the several intermediates.