Total synthesis of N-malayamycin A and related bicyclic purine and pyrimidine nucleosides.
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.
Hanessian
Stephen
S
Department of Chemistry, Université de Montréal, C. P. 6128, Succ. Centre-Ville, Montréal, P. Q., Canada H3C 3J7. stephen.hanessian@umontreal.ca
Huang
Guobin
G
Chenel
Caroline
C
Machaalani
Roger
R
Loiseleur
Olivier
O
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D019906:Nuclear Magnetic Resonance, Biomolecular; D009705:Nucleosides / Q000138:chemical synthesis*; D011684:Purine Nucleosides / Q000138:chemical synthesis*; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D016339:Spectrometry, Mass, Fast Atom Bombardment
D019086:Bridged Bicyclo Compounds, Heterocyclic; D009705:Nucleosides; D011684:Purine Nucleosides; D011741:Pyrimidine Nucleosides; C493874:malayamycin A