A Highly Convergent Total Synthesis of Leustroducsin B | Zendy

Barry M. Trost | Zendy; Bérenger Biannic | Zendy; Cheyenne S. Brindle | Zendy; B. Michael O’Keefe | Zendy; Thomas J. Hunter | Zendy; MingYu Ngai | Zendy

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A Highly Convergent Total Synthesis of Leustroducsin B

Author(s) -

Barry M. Trost,

Bérenger Biannic,

Cheyenne S. Brindle,

B. Michael O’Keefe,

Thomas J. Hunter,

MingYu Ngai

Publication year - 2015

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.5b07438

Subject(s) - chemistry , aldol reaction , total synthesis , ketone , tsuji–trost reaction , palladium , catalysis , molecule , alkylation , stereochemistry , allylic rearrangement , zinc , zincate , chelation , combinatorial chemistry , organic chemistry

Leustroducsin B exhibits a large variety of biological activities and unique structural features. An efficient and highly convergent total synthesis of Leustroducsin B was achieved in 17 longest linear and 39 total steps by disconnecting the molecule into three fragments having similar levels of complexity. These pieces were connected via a highly efficient chelate-controlled addition of a vinyl zincate to an α-hydroxy ketone and a silicon-mediated cross-coupling. The stereochemistry of the central and western fragments was set catalytically in high yields and excellent de by a zinc-ProPhenol-catalyzed aldol reaction and a palladium-catalyzed asymmetric allylic alkylation.

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