Biomimetic total syntheses of (-)-TAN1251A, (+)-TAN1251B, (+)-TAN1251C, and (+)-TAN1251D.
[reaction: see text] 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).
Snider
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BB
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02254-9110, USA. snider@brandeis.edu
Lin
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H
D018716:Molecular Mimicry; D018727:Muscarinic Antagonists / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010407:Penicillium / Q000737:chemistry; D013237:Stereoisomerism
D018727:Muscarinic Antagonists