Download PDF
Synfacts 2009(6): 0591-0591  
DOI: 10.1055/s-0029-1216669
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Aspidophytine

Contributor(s): Philip Kocienski, Indu Dager
K. C. Nicolaou*, S. M. Dalby, U. Majumder
The Scripps Research Institute, La Jolla and University of California, San Diego, USA
Further Information

Publication History

Publication Date:
25 May 2009 (online)

    Permissions and Reprints

Significance

Aspidophytine is one component of the insecticidal dimeric indole alkaloid haplophy­tine and was first obtained along with canthiphy­tine by an acid-mediated degradation of haplophytine. This concise total synthesis is built on three key reactions: (1) a triflic anhydride-mediated Vilsmeier-Haack reaction, (2) a radical cyclization (J → K), and (3) an oxidative lactonization of K.