Asymmetric Formal Synthesis of (+)-Lactacystin

被引：6

作者：

Sridhar, Chirumarry ^{[1
]}

Vijaykumar, Bodduri V. D. ^{[1
,2
]}

Radhika, Laghuvarapu ^{[1
]}

Shin, Dong-Soo ^{[2
]}

Chandrasekhar, Srivari ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Nat Prod Chem, Hyderabad 500007, Andhra Pradesh, India

[2] Changwon Natl Univ, Dept Chem, Chang Won 641773, GN, South Korea

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 30期

基金：

新加坡国家研究基金会;

关键词：

Natural products; Lactams; Asymmetric synthesis; Epoxidation; Chiral resolution; Palladium; ENANTIOSELECTIVE TOTAL SYNTHESES; PROTEASOME INHIBITOR; MICROBIAL METABOLITE; RADICAL CYCLIZATION; EFFICIENT SYNTHESIS; BETA-LACTONE; LACTACYSTIN; INTERMEDIATE; ROUTE; DEGRADATION;

D O I：

10.1002/ejoc.201402700

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：6707 / 6712

页数：6

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