Total Synthesis of (R)‑Sarkomycin Methyl Ester via Regioselective Intermolecular Pauson–Khand Reaction and Iridium-Catalyzed Asymmetric Isomerization

A new five-step enantioselective synthesis of (R)-sarkomycin methyl ester is described. The cyclopentane scaffold was built by a regioselective intermolecular Pauson–Khand reaction. Enantioselectivity was introduced by a novel Ir-catalyzed isomerization reaction. The last steps involved a catalytic...

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Bibliographic Details
Published in:Organic letters 2018-07, Vol.20 (13), p.3953-3957
Main Authors: Cabré, Albert, Khaizourane, Héléa, Garçon, Martí, Verdaguer, Xavier, Riera, Antoni
Format: Article
Language:English
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Summary:A new five-step enantioselective synthesis of (R)-sarkomycin methyl ester is described. The cyclopentane scaffold was built by a regioselective intermolecular Pauson–Khand reaction. Enantioselectivity was introduced by a novel Ir-catalyzed isomerization reaction. The last steps involved a catalytic hydrogenation of the exocylic double bond, followed by the deprotection and elimination of the amino group. This route is the shortest enantioselective synthesis of this antibiotic reported to date.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01525