Kenan and Caudill Laboratories of Chemistry, University of North Carolina at Chapel Hill, North Carolina 27599, USA.
Org Lett. 2010 Sep 3;12(17):3890-3. doi: 10.1021/ol1015898.
A convergent synthesis of the C31-C52 bis-tetrahydropyran core of the natural product amphidinol 3 is reported. A common intermediate was synthesized from d-tartaric acid utilizing an asymmetric glycolate alkylation/ring-closing metathesis sequence to construct the THP rings. Differential elaboration of the common intermediate allowed the synthesis of two distinct coupling partners which were joined through a modified Horner-Wadsworth-Emmons olefination to provide the bis-tetrahydropyran core.
报道了天然产物 Amphidinol 3 的 C31-C52 双四氢吡喃核心的收敛合成。利用不对称甘醇酸烷基化/环 closing metathesis 序列，从 d-酒石酸合成了一个共同的中间体，以构建 THP 环。共同中间体的差异修饰允许合成两个不同的偶联物，它们通过改良的 Horner-Wadsworth-Emmons 烯烃化反应连接，提供双四氢吡喃核心。
