Concise total synthesis of (±)-aspidospermidine

Haichen Ma; Xingang Xie; Peng Jing; Weiwei Zhang; Xuegong She

doi:10.1039/c5ob00228a

Concise total synthesis of (±)-aspidospermidine

Org Biomol Chem. 2015 May 14;13(18):5255-9. doi: 10.1039/c5ob00228a.

Authors

Haichen Ma¹, Xingang Xie, Peng Jing, Weiwei Zhang, Xuegong She

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, People's Republic of China. shexg@lzu.edu.cn.

PMID: 25856579
DOI: 10.1039/c5ob00228a

Abstract

(±)-Aspidospermidine (1) has been synthesized from the commercially available 2,3-dihydro-1H-carbazol-4(9H)-one 6 in 10 steps with 20% overall yield. The key step of the strategy is a one-pot carbonyl reduction/iminium formation/intramolecular conjugate addition reaction that may be applied for the synthesis of other Aspidosperma alkaloids.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbon-13 Magnetic Resonance Spectroscopy
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Proton Magnetic Resonance Spectroscopy
Quinolines / chemical synthesis*
Quinolines / chemistry
Spectrometry, Mass, Electrospray Ionization
Stereoisomerism

Substances

Indole Alkaloids
Quinolines
aspidospermidine