Beijing National Laboratory for Molecular Science-BNLMS, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100191, China.
Molecules. 2013 Jun 7;18(6):6723-33. doi: 10.3390/molecules18066723.
Protected L-homoDMDP en-8 and its C-6 epimer en-7 were prepared through two different pathways starting from the vinylpyrrolidine en-9. Based on the NMR and X-ray analysis, the stereochemistry of homoDMDP at C-6 was confirmed to be consistent with reported data. Compounds en-7 and en-8 are general intermediates for the synthesis of a series of 6-C-alkylated DMDP-related natural products, such as broussonetine G, homoDMDP-7-O-apioside, homoDMDP-7-O-b-D-xyloside and so on.
通过两种不同的途径，从乙烯基吡咯烷 en-9 开始制备了受保护的 L-homoDMDP en-8 和其 C-6 差向异构体 en-7。基于 NMR 和 X 射线分析，确定了 homoDMDP 在 C-6 处的立体化学与报道的数据一致。化合物 en-7 和 en-8 是一系列 6-C-烷基化 DMDP 相关天然产物，如布罗森通宁 G、homoDMDP-7-O-芹糖基-β-D-吡喃糖苷、homoDMDP-7-O-β-D-木糖苷等合成的通用中间体。
