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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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
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Language:English
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Asymmetric synthesis
Chiral resolution
Epoxidation
Lactams
Natural products
Palladium
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description 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.
doi_str_mv 10.1002/ejoc.201402700
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subjects Asymmetric synthesis
Chiral resolution
Epoxidation
Lactams
Natural products
Palladium
title Asymmetric Formal Synthesis of (+)-Lactacystin
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