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Synthesis 2005(19): 3380-3388  
DOI: 10.1055/s-2005-918474
PAPER
© Georg Thieme Verlag Stuttgart · New York

Scalable Synthesis of a Mycosamine Donor. Overcoming Difficult Reactivity in Allose Systems

Jeffrey M. Manthorpe, Alex M. Szpilman, Erick M. Carreira*
Laboratorium für Organische Chemie, ETH Hönggerberg, 8093 Zürich, Switzerland
Fax: +41(44)6321328; e-Mail: carreira@org.chem.ethz.ch;
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Publication History

Received 14 September 2005
Publication Date:
14 November 2005 (online)

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Abstract

Mycosamine is a dideoxyaminosugar found in medicinally relevant macrolides, including amphotericin B and nystatin. Herein we report a reliable, high yielding, scalable synthesis of a mycosamine donor. A major goal of our approach was to minimize purifications via judicious selection of protecting groups; the inherent properties of the allose framework created some deprotection obstacles that were ultimately solved.

Key words

asymmetric synthesis - natural products - glycosylations - protecting groups - medicinal chemistry

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