Enantioselective total synthesis of pyrinodemin A

Pyrinodemin A 1, a cytotoxic marine alkaloid, was synthesized in a convergent and enantioselective fashion. The key steps are an asymmetric intramolecular dipolar cycloaddition of an oxazoline N-oxide to introduce the bicyclic ring system of the molecule, a cuprate coupling for the extension of the...

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Veröffentlicht in:	Organic & biomolecular chemistry 2008-01, Vol.6 (8), p.1502-1510
Hauptverfasser:	Pouilhès, Annie, Amado, Anel Florès, Vidal, Anne, Langlois, Yves, Kouklovsky, Cyrille
Format:	Artikel
Sprache:	eng
Schlagworte:	Molecular Conformation Oxazoles - chemical synthesis Oxazoles - chemistry Pyridines - chemical synthesis Pyridines - chemistry Stereoisomerism
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creator	Pouilhès, Annie Amado, Anel Florès Vidal, Anne Langlois, Yves Kouklovsky, Cyrille
description	Pyrinodemin A 1, a cytotoxic marine alkaloid, was synthesized in a convergent and enantioselective fashion. The key steps are an asymmetric intramolecular dipolar cycloaddition of an oxazoline N-oxide to introduce the bicyclic ring system of the molecule, a cuprate coupling for the extension of the saturated chain and a B-alkyl Suzuki coupling for the introduction of a 3-pyridyl moiety. Reductive amination allowed the coupling of the second side-chain onto the nitrogen atom to give 1. Additionally, attempts to prepare 1 from a trienic precursor by a double B-alkyl Suzuki reaction are described.
doi_str_mv	10.1039/b800840j
format	Article
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source	MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Molecular Conformation Oxazoles - chemical synthesis Oxazoles - chemistry Pyridines - chemical synthesis Pyridines - chemistry Stereoisomerism
title	Enantioselective total synthesis of pyrinodemin A
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