Details

Autor(en) / Beteiligte

• Hanessian, Stephen
• Huang, Guobin
• Chenel, Caroline
• Machaalani, Roger
• Loiseleur, Olivier

Titel

Total Synthesis of N-Malayamycin A and Related Bicyclic Purine and Pyrimidine Nucleosides

Ist Teil von

• Journal of organic chemistry, 2005-08, Vol.70 (17), p.6721-6734

Ort / Verlag

Washington, DC: American Chemical Society

Erscheinungsjahr

2005

Link zum Volltext

Quelle

MEDLINE

Beschreibungen/Notizen

• 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.