Efficient Synthesis of [3H]-Sanglifehrin A via Selective Oxidation/Reduction of Alcohols at C31 and C35
The Journal of Organic Chemistry2005Vol. 70(23), pp. 9588–9590
Citations Over Time
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.
Related Papers
- → Robot Assisted Fracture Reduction(2008)24 cited
- Attribute Reduction Algorithm Based on Reduction Pruning(2007)
- → Novel Approaches to Knowledge Reduction in Inconsistent Decision Systems(2006)1 cited
- Effect of the Reduction on Centerline Segregation of Steel(2009)
- → ИСПОЛЬЗОВAНИЕ ПОТЕНЦИAЛA СОЦИAЛЬНЫХ ПAРТНЕРОВ В ПОДГОТОВКЕ БУДУЩИХ ПЕДAГОГОВ(2024)