Tetrahedron Letters

A new and efficient asymmetric synthesis of oseltamivir phosphate (Tamiflu) from D-mannose

N Chuanopparat, N Kongkathip, B Kongkathip

Index: Chuanopparat, Nutthawat; Kongkathip, Ngampong; Kongkathip, Boonsong Tetrahedron Letters, 2012 ,  vol. 53,  # 46  p. 6209 - 6211,3

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Citation Number: 6

Abstract

Oseltamivir phosphate (Tamiflu) was synthesized from d-mannose through a short and practical synthetic route. A unique feature of the route is that the bulky 3-pentyloxy group and adjacent acetamide of Tamiflu were introduced at an early stage of the synthesis by copper- catalyzed regioselective ring-opening of the 2, 3-pentylidene ketal of d-lyxofuranoside. The d-lyxofuranoside ethylphosphonate precursor was then cyclized via an intramolecular ...