Tetrahedron Letters

Diastereoselective concise syntheses of the polyhydroxylated alkaloids DMDP and DAB

ME Bouillon, SG Pyne

Index: Bouillon, Marc E.; Pyne, Stephen G. Tetrahedron Letters, 2014 , vol. 55, # 2 p. 475 - 478

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Citation Number: 12

Abstract

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 ...

~99%

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