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A Highly Convergent Total Synthesis of Leustroducsin B.

ABSTRACT: 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.

SUBMITTER: Trost BM

PROVIDER: S-EPMC4621997 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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A Highly Convergent Total Synthesis of Leustroducsin B.

Trost Barry M BM Biannic Berenger B Brindle Cheyenne S CS O'Keefe B Michael BM Hunter Thomas J TJ Ngai Ming-Yu MY

Journal of the American Chemical Society 20150901 36

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 cent ...[more]

PMID: 26313159

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