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Literature DB >> 19746925

Enantioselective synthesis of the R-enantiomer of the feeding deterrent (S)-ypaoamide.

Jie Chen¹, Pei-Qiang Huang, Yves Queneau.

Abstract

The enantioselective synthesis of the R-enantiomer of the marine natural product (S)-ypaoamide (5) is reported. The synthesis features both a flexible racemization-free approach to the 5-substituted 3-pyrrolin-2-one segment, and a lipase (CCL)-promoted deacetylation reaction to reach the orthogonal deprotection. Through this work the absolute configuration of the natural ypaoamide was determined as S.

Entities: Chemical Gene

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Year: 2009 PMID： 19746925 DOI： 10.1021/jo901557h

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

5 in total

1. Enantioselective rhodium-catalyzed isomerization of 4-iminocrotonates: asymmetric synthesis of a unique chiral synthon.

Authors: Wen-Zhen Zhang; John C K Chu; Kevin M Oberg; Tomislav Rovis
Journal: J Am Chem Soc Date: 2015-01-12 Impact factor: 15.419

5. A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins.

Authors: Nianhong Lu; Lihong Wang; Zhanshan Li; Wei Zhang
Journal: Beilstein J Org Chem Date: 2012-02-06 Impact factor: 2.883

5 in total

Enantioselective synthesis of the R-enantiomer of the feeding deterrent (S)-ypaoamide.

1. Enantioselective rhodium-catalyzed isomerization of 4-iminocrotonates: asymmetric synthesis of a unique chiral synthon.

2. Synthesis of functionalized dihydro-2-oxopyrroles using graphene oxide as heterogeneous catalyst.

Review 3. The chemical ecology of cyanobacteria.

4. Ring-Expansion Approaches for the Total Synthesis of Salimabromide.

5. A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins.