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Synfacts 2010(1): 0001-0001
DOI: 10.1055/s-0029-1218392
DOI: 10.1055/s-0029-1218392
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (+)-Haplophytine
Contributor(s):Philip KocienskiK. C. Nicolaou*, S. M. Dalby, S. Li, T. Suzuki, D. Y.-K. Chen*
Institute of Chemical and Engineering Sciences, A*STAR, Singapore; The Scripps Research Institute, La Jolla and University of California, San Diego, USA
Total Synthesis of (+)-Haplophytine
Angew. Chem. Int. Ed. 2009, 48: 7752-7756
Institute of Chemical and Engineering Sciences, A*STAR, Singapore; The Scripps Research Institute, La Jolla and University of California, San Diego, USA
Total Synthesis of (+)-Haplophytine
Angew. Chem. Int. Ed. 2009, 48: 7752-7756
Further Information
Publication History
Publication Date:
21 December 2009 (online)
Key words
haplophytine - oxidative coupling - Suzuki-Miyaura coupling - radical cyclization - semi-pinacol oxidative rearrangement
Significance
The first of the five quaternary centers in haplophytine was installed by an oxidative coupling reaction (A + B → C) mediated by phenyliodonium bis(trifluoroacetate) (PIFA).
Comment
The oxidative semi-pinacol rearrangement (D → E) was also used in Fukuyama’s synthesis of haplophytine (Angew. Chem. Int. Ed. 2009, 48, 7600; Synfacts 2010, 3). The lactone ring was created by an oxidative cyclization mediated by K3[Fe(CN)6].