Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 17, Pages 6721-6734Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo050727b
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[GRAPHICS] 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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