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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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Publication details

The article was received on 22 Oct 2019, accepted on 12 Nov 2019 and first published on 13 Nov 2019


Article type: Research Article
DOI: 10.1039/C9QO01292C
Org. Chem. Front., 2020, Advance Article

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    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, Advance Article , DOI: 10.1039/C9QO01292C

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