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

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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

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Supplementary files

Article information


Submitted
22 Oct 2019
Accepted
12 Nov 2019
First published
13 Nov 2019

Org. Chem. Front., 2020,7, 76-103
Article type
Research Article

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

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