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Molecules 2013, 18(6), 6723-6733; doi:10.3390/molecules18066723

General Intermediates for the Synthesis of 6-C-Alkylated DMDP-Related Natural Products

1
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
2
School of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, China
*
Author to whom correspondence should be addressed.
Received: 8 May 2013 / Revised: 24 May 2013 / Accepted: 27 May 2013 / Published: 7 June 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

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. View Full-Text
Keywords: homo-DMDP; broussonetine G; homoDMDP-7-O-apioside; glycosidase inhibitors; cyclic nitrones homo-DMDP; broussonetine G; homoDMDP-7-O-apioside; glycosidase inhibitors; cyclic nitrones
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Huang, M.-H.; Li, Y.-X.; Jia, Y.-M.; Yu, C.-Y. General Intermediates for the Synthesis of 6-C-Alkylated DMDP-Related Natural Products. Molecules 2013, 18, 6723-6733.

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