A Local Desymmetrization Approach to Piperidinyl Acetic Acid γ‑Secretase Modulators

A desymmetrization-based approach for the synthesis of piperidinyl acetic acid γ-secretase modulators has been developed. The synthetic sequence features the use of N-tert-butanesulfinyl imine reduction and a diastereoselective lactam formation to set up the chiral centers. The synthetic utility is...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 86; no. 21; pp. 15481 - 15487
Main Authors Cheng, Peng, Lu, Haigen, Zu, Liansuo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.11.2021
Amer Chemical Soc
Subjects
Acetic Acid
Amyloid Precursor Protein Secretases
Chemistry
Chemistry, Organic
Gamma Secretase Inhibitors and Modulators
Physical Sciences
Science & Technology
ASYMMETRIC-SYNTHESIS
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Summary:A desymmetrization-based approach for the synthesis of piperidinyl acetic acid γ-secretase modulators has been developed. The synthetic sequence features the use of N-tert-butanesulfinyl imine reduction and a diastereoselective lactam formation to set up the chiral centers. The synthetic utility is demonstrated by the concise asymmetric synthesis of γ-secretase modulator GSM-1.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01970