Synthetic studies on the perhydropyrrolo[2,1-j]quinoline marine alkaloids lepadiformine and cylindricine C using a 2-azapentadienyl anion cycloaddition. Synthesis of 2,13-diepilepadiformine (or 2-epi-11-deoxycylindricine C)

✍ Scribed by William H Pearson; Nancy S Barta; Jeff W Kampf

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 238 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00632-1

✦ Synopsis

Tin-lithium exchange of 13 with n-BuLi produced the 2-azapentadienyl anion 6 (R = CH3), which participated in a [rc4s+n2s] cycloaddition reaction with phenyl vinyl sulfide to afford the spirocyclic pyrrolidine 14, which as coverted to 2,13-diepilepadiformine (or 2-epi-11 -deoxycylindricine C) 17 by a sequence of steps involving oxidative cleavage of the propenyl side-chain, intramolecular reductive amination, and desulfurization.