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Synfacts 2009(9): 0944-0944  
DOI: 10.1055/s-0029-1217622
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Vinblastine

Contributor(s): Philip Kocienski
H. Ishikawa, D. A. Colby, S. Seto, P. Va, A. Tam, H. Kakei, T. J. Rayl, I. Hwang, D. L. Boger*
The Scripps Research Institute, La Jolla, USA
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Publication History

Publication Date:
21 August 2009 (online)

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Significance

A remarkably detailed mechanistic and labeling study was used to elucidate the mechanism of an iron(III)-promoted biomimetic synthesis of vinblastine. A key step is the inter­ception of the azabenzofulvene D by vindoline to generate the coupling product E with the correct stereochemistry at C16. The chemistry depicted was used to prepare a large number of analogues.