Asymmetric Formal Synthesis of (+)-Lactacystin

A formal synthesis of (+)‐lactacystin was achieved from commercially available isobutyraldehyde and ethyl acrylate. A Baylis–Hillman reaction, an intermolecular nucleophilic displacement under Mitsunobu conditions, a Sharpless asymmetric epoxidation, a palladium(0)‐catalyzed syn‐selective ring openi...

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Bibliographic Details
Published in:European journal of organic chemistry 2014-10, Vol.2014 (30), p.6707-6712
Main Authors: Sridhar, Chirumarry, Vijaykumar, Bodduri V. D., Radhika, Laghuvarapu, Shin, Dong-Soo, Chandrasekhar, Srivari
Format: Article
Language:English
Subjects:
Asymmetric synthesis
Chiral resolution
Epoxidation
Lactams
Natural products
Palladium
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Summary:A formal synthesis of (+)‐lactacystin was achieved from commercially available isobutyraldehyde and ethyl acrylate. A Baylis–Hillman reaction, an intermolecular nucleophilic displacement under Mitsunobu conditions, a Sharpless asymmetric epoxidation, a palladium(0)‐catalyzed syn‐selective ring opening of an epoxide by treatment with an azide, a one‐pot azide reductive lactamization, and a ruthenium‐catayzed oxidation were employed as the key steps. A formal synthesis of (+)‐lactacystin was achieved from readily available isobutyraldehyde and ethyl acrylate by using a Baylis–Hillman reaction, an intermolecular nucleophilic displacement under Mitsunobu conditions, a Sharpless asymmetric epoxidation, a palladium‐catalyzed syn‐selective ring opening of an epoxide, an azide reductive lactamization, and a ruthenium‐catalyzed oxidation as the key steps.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201402700