Nucleic acids U 0700Total Synthesis of N-Malayamycin A (I) and Related Bicyclic Purine and Pyrimidine Nucleosides. -The title compounds are prepared in order to test their biological activity. -(HANESSIAN*, S.; HUANG, G.; CHENEL, C.; MACHAALANI, R.; LOISELEUR, O.; J. Org. Chem. 70 (2005) 17, 6721-6734; Dep. Chem., Univ. Montreal, Montreal, Que. H3C 3J7, Can.; Eng.) -Jannicke 52-184
[reaction: see text] The stereocontrolled synthesis of malayamycin A, a novel naturally occurring bicyclic C-nucleoside of the perhydrofuropyran type, is described.
Methods are described for the total synthesis of bicyclic perhydrofuropyran nucleosides as N-analogues of the naturally occurring malayamycin A. Formation of the N-nucleosides relied on the activation of thioglycosides, proceeding via sulfonium intermediates. Ring closure metathesis was used in two approaches to build the bicyclic dioxa heterocycle. Another approach relied on the use of a sugar precursor and cyclization to the bicyclic thioglycoside.
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