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Biomimetic Total Syntheses of (−)-TAN1251A, (+)-TAN1251B, (+)-TAN1251C, and (+)-TAN1251D
Journal article   Peer reviewed

Biomimetic Total Syntheses of (−)-TAN1251A, (+)-TAN1251B, (+)-TAN1251C, and (+)-TAN1251D

Barry B Snider and Hong Lin
Organic letters, Vol.2(5), pp.643-646
03/09/2000
DOI: https://doi.org/10.1021/ol991401q
PMID: 10814399

Abstract

The muscarinic antagonists (−)-TAN1251A (1), (+)-TAN1251B (2), (+)-TAN1251C (3), and (+)-TAN1251D (4) have been synthesized biomimetically by enamine formation from an amino aldehyde to give TAN1251C ketal 18. Oxidation and reduction lead to TAN1251A (1), which has been hydroxylated to give TAN1251B (2). Stereospecific reduction of TAN1251C ketal 18 leads to TAN1251D (4).

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