Title

Diastereoselective concise syntheses of the polyhydroxylated alkaloids DMDP and DAB

RIS ID

86085

Publication Details

Bouillon, M. & Pyne, S. G. (2014). Diastereoselective concise syntheses of the polyhydroxylated alkaloids DMDP and DAB. Tetrahedron Letters, 55 (2), 475-478.

Abstract

A diastereoselective concise synthesis of the iminosugars DMDP and DAB is presented starting from l-xylose and affording the two alkaloids in good yields of 35% and 22% over seven and eight steps, respectively. The Petasis borono-Mannich reaction of 3,5-di-O-benzyl-l-xylofuranose with benzylamine and (E)-styrylboronic acid served as the nitrogen-introducing key step furnishing the new C-N bond in an entirely diastereoselective manner. A chemo- and regioselective O-mesylation followed by an intramolecular SN2-cyclisation allowed the formation of the pyrrolidine ring. Ozonolysis of the styryl double bond and subsequent reduction to form the C-5 hydroxymethyl substituent followed by hydrogenolysis of the benzyl protecting groups concluded the DMDP synthesis. Furthermore, an unexpected fragmentation process during the ozonolysis reaction also gave access to the C-5 decarbinolated DMDP derivative DAB.

Grant Number

ARC/DP1094518

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