Total Syntheses of Lycopodium Alkaloids (+)-Fawcettimine, (+)-Fawcettidine, and (−)-8-Deoxyserratinine

Authors


  • We thank Prof. David Zhigang Wang (Peking University Shenzhen Graduate School) and Dr. Shaohui Wang for helpful discussions, Mingyan Zhao and Rui Liu (NIBS) for NMR and HPLC-MS analysis, and Dr. Jiang Zhou (Peking University) for HRMS analysis. Financial support from the National High Technology Projects 863 (2008AA022317), the Program for New Century Excellent Talents in University (NCET-10-0614), and the NSFC (20802050, 21072150) is gratefully acknowledged.

Abstract

original image

A shared story: Three fawcettimine- and serratinine-type Lycopodium alkaloids are prepared from a common tetracyclic spirodiketone intermediate in concise total syntheses (see scheme). The intermediate was constructed by a remarkable biosynthesis-inspired transannular N[BOND]C bond formation to the spiro-configured carbon center and a hydroxy-directed pinacol coupling promoted by SmI2.

Ancillary