Enantioselective total synthesis of (+)-SCH 351448

被引：20

作者：

Crimmins, Michael T. ^{[1
]}

Vanier, Grace S. ^{[1
]}

机构：

[1] Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 13期

关键词：

D O I：

10.1021/ol061073b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of SCH 351448 has been completed. Twelve of the fourteen stereogenic centers were established through chiral enolate reactions, and six key C-C bonds were formed by metathesis reactions.

引用

页码：2887 / 2890

页数：4

共 15 条

[1] Selective synthesis of the para-quinone region of geldanamycin [J].

Andrus, MB ;

Hicken, EJ ;

Meredith, EL ;

Simmons, BL ;

Cannon, JF .

ORGANIC LETTERS, 2003, 5 (21) :3859-3862

[2] Efficient asymmetric synthesis of (+)-SCH 351448 [J].

Bolshakov, S ;

Leighton, JL .

ORGANIC LETTERS, 2005, 7 (17) :3809-3812

[3] A RECEPTOR-MEDIATED PATHWAY FOR CHOLESTEROL HOMEOSTASIS [J].

BROWN, MS ;

GOLDSTEIN, JL .

SCIENCE, 1986, 232 (4746) :34-47

[4] A general model for selectivity in olefin cross metathesis [J].

Chatterjee, AK ;

Choi, TL ;

Sanders, DP ;

Grubbs, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370

[5] Titanium enolates of thiazolidinethione chiral auxiliaries: Versatile tools for asymmetric aldol additions [J].

Crimmins, MT ;

Chaudhary, K .

ORGANIC LETTERS, 2000, 2 (06) :775-777

[6] Diastereoselective alkylations of oxazolidinone glycolates: A useful extension of the Evans asymmetric alkylation [J].

Crimmins, MT ;

Emmitte, KA ;

Katz, JD .

ORGANIC LETTERS, 2000, 2 (14) :2165-2167

[7] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[8] Practical and highly selective oxazolidinethione-based asymmetric acetate aldol reactions with aliphatic aldehydes [J].

Guz, NR ;

Phillips, AJ .

ORGANIC LETTERS, 2002, 4 (13) :2253-2256

[9] A novel microbial metabolite, activator of low density lipoprotein receptor promoter [J].

Hegde, VR ;

Puar, MS ;

Dai, P ;

Patel, M ;

Gullo, VP ;

Das, PR ;

Bond, RW ;

McPhail, AT .

TETRAHEDRON LETTERS, 2000, 41 (09) :1351-1354

[10] Stereoselective synthesis of (+)-SCH 351448: A unique ligand system for sodium, calcium, and other cations [J].

Kang, EJ ;

Cho, EJ ;

Ji, MK ;

Lee, YE ;

Shin, DM ;

Choi, SY ;

Chung, YK ;

Kim, JS ;

Kim, HJ ;

Lee, SG ;

Lah, MS ;

Lee, E .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6321-6329

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