Issue 1, 2020

A diastereoselective approach to amino alcohols and application for divergent synthesis of dolastatin 10

Abstract

A diastereoselective approach to obtain amino alcohols 10 through SmI2-induced radical addition of chiral imine 8 with 2-(benzyloxymethylsulfonyl)pyridine 9 is described. This approach was easily used for the synthesis of non-natural amino acid 15, a flexible key fragment whose utility was demonstrated in the divergent synthesis of dolastatin 10 (1) and its nine analogues 31a, 31c, 31d, 31e, 31f, 31g, 40a, 40b and 40c were obtained.

Graphical abstract: A diastereoselective approach to amino alcohols and application for divergent synthesis of dolastatin 10

Supplementary files

Article information

Article type
Research Article
Submitted
22 Oct 2019
Accepted
12 Nov 2019
First published
13 Nov 2019

Org. Chem. Front., 2020,7, 76-103

A diastereoselective approach to amino alcohols and application for divergent synthesis of dolastatin 10

X. Nie, Z. Mao, W. Zhou, C. Si, B. Wei and G. Lin, Org. Chem. Front., 2020, 7, 76 DOI: 10.1039/C9QO01292C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements