Concise Total Synthesis of (±)-Aspidospermidine

SHE Xuegong; MA Haichen; XIE Xingang; ZHANG weiwei

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Concise Total Synthesis of (±)-Aspidospermidine

SHE Xuegong * #,MA Haichen,XIE Xingang,ZHANG weiwei

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China

*Correspondence author

#Submitted by

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Funding: Specialized Research Fund for the Doctoral Program of Higher Education （No.20130211110018）

Opened online: 5 January 2015

Accepted by: none

Citation: SHE Xuegong,MA Haichen,XIE Xingang.Concise Total Synthesis of (±)-Aspidospermidine[OL]. [ 5 January 2015] http://en.paper.edu.cn/en_releasepaper/content/4625889

Aspidosperma alkaloids, which comprise more than 250 members, share a common pentacyclic skeleton imbedded in an indoline substructure and many of which have significant biological activities. The unique structure and diverse bioactivities of Aspidosperma alkaloids have attracted much attention of the synthetic community for many years and have remained a focus on extensive research activities to present day. Aspidospermidine (1) was isolated from the leaves and skin of Apocynaceae plants and contains a typical skeleton of indole alkaloids. It also exhibits significantly respiratory stimulant and antibiotic activities. The fundamental structure has been the primary target for most of the efforts toward Aspidosperma alkaloids syntheses and has served as the ideal test case for recent developed synthetic strategies. In this paper (±)-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. Key step of the strategy is a one-pot carbonyl reduction / iminium formation / intramolecular conjugate addition reaction that may be applied for synthesis of other kind of Aspidosperma alkaloids.

Keywords:Natural products; Total synthesis; Aspidosperma alkaloids; Biological activity

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