Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts 02115, USA.
Org Lett. 2010 Sep 3;12(17):3752-5. doi: 10.1021/ol101340n.
A total synthesis of the fostriecin has been achieved in 24 steps from enyne 11. The lactone moiety was installed by a Leighton allylation and Grubbs ring-closing metathesis reaction. The highly reactive Z,Z,E-triene moiety was installed via a late-stage Suzuki-Miyaura cross-coupling of a remarkably stable Z-vinyl boronate. The relative and absolute stereocenters of the C-8,9,11 triol were generated with a regio- and stereoselective asymmetric hydration/oxidation sequence.
已通过从烯炔 11 出发经 24 步反应实现了 fostriecin 的全合成。内酯部分通过 Leighton 烯丙基化和 Grubbs 闭环复分解反应构建。通过高度反应性的 Z,Z,E-三烯基在后期阶段的 Suzuki-Miyaura 交叉偶联反应，使用非常稳定的 Z-乙烯基硼酸酯来引入三烯部分。C-8、9、11 三醇的相对和绝对立体中心通过区域和立体选择性不对称水合/氧化序列生成。
