Ti-Catalyzed Cross-Cyclomagnesiation of 1,2-Dienes in the Total Z,Z,Z-Stereoselective Synthesis of Natural Acetogenin–Chatenaytrienin-1 | Zendy

Vladimir A. D’yakonov | Zendy; Regina A. Tuktarova | Zendy; У. М. Джемилев | Zendy

Open Access

Ti-Catalyzed Cross-Cyclomagnesiation of 1,2-Dienes in the Total Z,Z,Z-Stereoselective Synthesis of Natural Acetogenin–Chatenaytrienin-1

Author(s) -

Vladimir A. D’yakonov,

Regina A. Tuktarova,

У. М. Джемилев

Publication year - 2019

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.9b01951

Subject(s) - acetogenin , tetrahydropyran , stereoselectivity , total synthesis , yield (engineering) , catalysis , chemistry , acetal , stereochemistry , ring (chemistry) , organic chemistry , physics , biology , botany , thermodynamics , annonaceae

The first total synthesis of natural acetogenin, chatenaytrienin-1, was performed in 10 steps and in 41% overall yield using cross-cyclomagnesiation of (6 Z )-heptadeca-1,2,6-triene and trideca-11,12-dien-1-ol tetrahydropyran acetal with EtMgBr in the presence of Mg metal and the Cp 2 TiCl 2 catalyst (10 mol %) as the key step of the synthesis.

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