A Highly Convergent Total Synthesis of Leustroducsin B

作者:Trost Barry M*; Biannic Berenger; Brindle Cheyenne S; O'Keefe B Michael; Hunter Thomas J; Ngai Ming Yu
来源:Journal of the American Chemical Society, 2015, 137(36): 11594-11597.
DOI:10.1021/jacs.5b07438

摘要

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 a-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.

  • 出版日期2015-9-16