Kozmin S A
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
Org Lett. 2001 Mar 8;3(5):755-8. doi: 10.1021/ol015514x.
[structure: see text]. A complete relay of the initial stereochemical information is central to the efficient and highly stereocontrolled construction of the C1-C15 fragment of the marine macrolide leucascandrolide A. Cyclic silane 3, assembled via Pt-catalyzed hydrosilylation, was designed to serve as a temporary template for the installation of the C12 stereogenic center. The strategy features a highly convergent C10-C11 bond construction via 1,5-anti-selective aldol reaction and rapid assembly of the trisubstituted pyran subunit via Prins desymmetrization.
[结构：见正文]。初始立体化学信息的完整传递对于海洋大环内酯类化合物白藜芦醇A的C1-C15片段的高效且高度立体控制的构建至关重要。通过铂催化的硅氢化反应组装的环状硅烷3被设计用作安装C12立体中心的临时模板。该策略的特点是通过1,5-反式选择性羟醛反应进行高度汇聚的C10-C11键构建，以及通过普林斯去对称化快速组装三取代的吡喃亚基。
