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Synfacts 2010(1): 0003-0003
DOI: 10.1055/s-0029-1218265
DOI: 10.1055/s-0029-1218265
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (+)-Haplophytine
Contributor(s):Philip KocienskiH. Ueda, H. Satoh, K. Matsumoto, K. Sugimoto, T. Fukuyama*, H. Tokuyama*
Tohoku University, Sendai and University of Tokyo, Japan
Total Synthesis of (+)-Haplophytine
Angew. Chem. Int. Ed. 2009, 48: 7600-7603
Tohoku University, Sendai and University of Tokyo, Japan
Total Synthesis of (+)-Haplophytine
Angew. Chem. Int. Ed. 2009, 48: 7600-7603
Further Information
Publication History
Publication Date:
21 December 2009 (online)
Key words
haplophytine - indole alkaloids - Fischer indole synthesis - Friedel-Crafts alkylation - quaternary centers
Significance
The first total synthesis of haplophytine features a Friedel-Crafts alkylation to create the quaternary center in D and an oxidative rearrangement F → G → H.
Comment
The stereogenic center in tetrahydro-β-carboline A was installed via a Noyori asymmetric hydrogenation. The Fischer indole synthesis gave two regioisomers (5:3, K major).