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Efficient synthesis of [3H]-sanglifehrin A via selective oxidation/reduction of alcohols at C31 and C35.

Wagner, Juergen and Andres, Hendrik and Rohrbach, Stefan and Wagner, Dieter and Oberer, Lukas and France, Julien (2005) Efficient synthesis of [3H]-sanglifehrin A via selective oxidation/reduction of alcohols at C31 and C35. The Journal of Organic Chemistry, 70 (23). pp. 9588-9590. ISSN 0022-3263

Abstract

[Reaction: see text]. Sanglifehrin A is a novel complex natural product showing strong immunosuppressive activity and remarkably high affinity for cyclophilin A. To assess its pharmacokinetic properties in vivo, an efficient synthetic route was developed to introduce a tritium label in position C35 of sangliferin A via an oxidation/reduction strategy. The synthetic approach is particularly attractive, because the C35-oxo intermediate 7 is available in good yield on large scale and the reducing agent, lithium tri-sec-butylborotritide, is readily available. An attempt to apply a similar strategy to the alcohol in position C31 led primarily to C31-epi-hydroxy sanglifehrin A under a variety of conditions.

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Date Deposited: 14 Dec 2009 13:59
Last Modified: 31 Jan 2013 01:16
URI: https://oak.novartis.com/id/eprint/483

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