Tubulysin Synthesis Featuring Stereoselective Catalysis and Highly Convergent Multicomponent Assembly | Zendy

T. M. Vishwanatha | Zendy; Ben N. G. Giepmans | Zendy; Sayed K. Goda | Zendy; Alexander Dömlingꝉ | Zendy

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Tubulysin Synthesis Featuring Stereoselective Catalysis and Highly Convergent Multicomponent Assembly

Author(s) -

T. M. Vishwanatha,

Ben N. G. Giepmans,

Sayed K. Goda,

Alexander Dömlingꝉ

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c01718

Subject(s) - chemistry , total synthesis , regioselectivity , yield (engineering) , stereoselectivity , combinatorial chemistry , convergent synthesis , modular design , catalysis , stereochemistry , organic chemistry , computer science , programming language , materials science , metallurgy

A concise and modular total synthesis of the highly potent N-desacetoxytubulysin H () has been accomplished in 18 steps in an overall yield of up to 30%. Our work highlights the complexity-augmenting and route-shortening power of diastereoselective multicomponent reaction (MCR) as well as the role of bulky ligands to perfectly control both the regioselective and diastereoselective synthesis of tubuphenylalanine in just two steps. The total synthesis not only provides an operationally simple and step economy but will also stimulate major advances in the development of new tubulysin analogues.

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