A novel convergent method for the synthesis of α-acyl-γ-hydroxylactams and its application in the total synthesis of PI-090 and 091

A novel convergent method for the synthesis of α-acyl-γ-hydroxylactams utilizing the aldol reaction of N-Boc-protected γ-methoxylactams was developed. As the first application of this method for the synthesis of biologically active natural products, the total synthesis of platelet aggregation inhibi...

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Bibliographic Details
Published inBioorganic & medicinal chemistry letters Vol. 22; no. 14; pp. 4765 - 4768
Main Authors Uchiro, Hiromi, Shionozaki, Nobuhiro, Kobayakawa, Yu, Nakagawa, Hiroko, Makino, Kimiko
Format Journal Article
LanguageEnglish
Published Amsterdam Elsevier Ltd 15.07.2012
Elsevier
Subjects
Acylation
bioactive properties
Biological and medical sciences
Hydroxylation
lactams
Lactams - chemical synthesis
Medical sciences
Molecular Structure
Pharmacology. Drug treatments
PI-090
PI-091
platelet aggregation
Platelet aggregation inhibitor
Total synthesis
α-Acyl-γ-hydroxylactam
Platelet aggregation inhibitor
PI-091
α-Acyl-γ-hydroxylactam
PI-090
Total synthesis
Anticoagulant
Chemical synthesis
Antiplatelet agent
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Summary:A novel convergent method for the synthesis of α-acyl-γ-hydroxylactams utilizing the aldol reaction of N-Boc-protected γ-methoxylactams was developed. As the first application of this method for the synthesis of biologically active natural products, the total synthesis of platelet aggregation inhibitors PI-090 and PI-091 were also investigated and successfully achieved.
Bibliography:http://dx.doi.org/10.1016/j.bmcl.2012.05.065
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2012.05.065