Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

There will be scheduled maintenance work beginning on Saturday 15th June 2019 at 8:30 am through to Sunday 16th June 2019 at 11:30 pm (BST).

During this time our website may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 29, 2017
Previous Article Next Article

A practical approach to asymmetric synthesis of dolastatin 10

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 08 Jun 2017, accepted on 29 Jun 2017 and first published on 29 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01395G
Org. Biomol. Chem., 2017,15, 6119-6131

  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements