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Issue 29, 2017
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A practical approach to asymmetric synthesis of dolastatin 10

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Abstract

Dolastatin 10, an antineoplastic agent for cancer chemotherapy, is a linear peptide possessing N,N-dimethyl Val-OH, L-valine, (3R,4S,5S)-dolaisoleucine, (2R,3R,4S)-dolaproine and (S)-dolaphenine. Our efficient synthesis includes the following three key features: (1) SmI2-induced cross-coupling was employed to couple aldehyde 11 with (S)-N-tert-butanesulfinyl imine 12 to generate the required stereocenters of Dap (7); (2) asymmetric addition of chiral N-sulfinyl imine 10 provided a straightforward approach to the synthesis of the protected Doe ((S,S)-8); (3) a practical method to the key subunit Val-Dil (24a) has been established as an alternative synthetic route for the synthesis of this challenging chemical structure.

Graphical abstract: A practical approach to asymmetric synthesis of dolastatin 10

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Supplementary files

Article information


Submitted
08 Jun 2017
Accepted
29 Jun 2017
First published
29 Jun 2017

Org. Biomol. Chem., 2017,15, 6119-6131
Article type
Paper

A practical approach to asymmetric synthesis of dolastatin 10

W. Zhou, X. Nie, Y. Zhang, C. Si, Z. Zhou, X. Sun and B. Wei, Org. Biomol. Chem., 2017, 15, 6119
DOI: 10.1039/C7OB01395G

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