General intermediates for the synthesis of 6-C-alkylated DMDP-related natural products.
writer：Huang, Mu-Hua Li, Yi-Xian Jia, Yue-Mei Yu, Chu-Yi.
keywords：DMDP broussonetine apioside glycosidase inhibitor prepn nitrone
source：期刊
specific source：Molecules
Issue time：2013年
Protected homoDMDP and a C-6 epimer were prepd. by two different pathways starting from a vinylpyrrolidine precursor. Based on the NMR and X-ray anal., the stereochem. of homoDMDP at C-6 was confirmed to be consistent with reported data. The above-mentioned compds. 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-β-xyloside and so on (no data). The title compds. thus formed included an oxazolidinone deriv. (I) and related substances and epimer. The synthesis of the target compds. was achieved using (2S,3S,4S,5S)-2-ethenyl-3,4-bis(phenylmethoxy)-5-[(phenylmethoxy)methyl]-1-pyrrolidinecarboxylic acid phenylmethyl ester and (2S,3S,4S,5S)-2-[(1R)-1,2-dihydroxyethyl]-3,4-bis(phenylmethoxy)-5-[(phenylmethoxy)methyl]-1-pyrrolidinecarboxylic acid phenylmethyl ester as starting materials. [on SciFinder(R)]