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

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

1,2, 1, 1 and 1,*
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.
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
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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