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

共 63 条

[1]

[Anonymous], ANGEW CHEM

[2] α,β-unsaturated β-silyl imide substrates for catalytic, enantioselective conjugate additions:: A total synthesis of (+)-lactacystin and the discovery of a new proteasome inhibitor [J].

Balskus, Emily P. ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6810-6812

[3] Progress toward the total synthesis of (+)-aldosterone: Synthesis of the A-D rings [J].

Bear, BR ;

Parnes, JS ;

Shea, KJ .

ORGANIC LETTERS, 2003, 5 (10) :1613-1616

[4] Formal synthesis of (+)-lactacystin based on a novel radical cyclisation of an α-ethynyl substituted serine [J].

Brennan, CJ ;

Pattenden, G ;

Rescourio, G .

TETRAHEDRON LETTERS, 2003, 44 (49) :8757-8760

[5] Total synthesis of (-)-lentiginosine [J].

Chandrasekhar, S. ;

Vijaykumar, B. V. D. ;

Pratap, T. V. .

TETRAHEDRON-ASYMMETRY, 2008, 19 (06) :746-750

[6] Poly(ethyleneglycol) (PEG): a rapid and recyclable reaction medium for the DABCO-catalyzed Baylis-Hillman reaction [J].

Chandrasekhar, S ;

Narsihmulu, C ;

Saritha, B ;

Sultana, SS .

TETRAHEDRON LETTERS, 2004, 45 (30) :5865-5867

[7] Enantioselective synthesis of (-)-lasubine II [J].

Chandrasekhar, S. ;

Murali, R. V. N. S. ;

Reddy, Ch. Raji .

TETRAHEDRON LETTERS, 2009, 50 (40) :5686-5688

[8] Stereoflexible total synthesis of (-)-epiquinamide [J].

Chandrasekhar, S. ;

Parida, Bibhuti Bhusan ;

Rambabu, Ch. .

TETRAHEDRON LETTERS, 2009, 50 (26) :3294-3295

[9] Total synthesis of hyacinthacine A1, a glycosidase inhibitor [J].

Chandrasekhar, Srivari ;

Parida, Bibhuti Bhusan ;

Rambabu, Chegondi .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) :7826-7828

[10] SYNTHESIS OF MONOPROTECTED 2-ALKYLIDENE-1,3-PROPANEDIOLS BY AN UNUSUAL S(N)2' MITSUNOBU REACTION [J].

CHARETTE, AB ;

COTE, B ;

MONROC, S ;

PRESCOTT, S .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6888-6894

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