Total synthesis of baccatin III and taxol

被引：406

作者：

Danishefsky, SJ ^{[1
]}

Masters, JJ ^{[1
]}

Young, WB ^{[1
]}

Link, JT ^{[1
]}

Snyder, LB ^{[1
]}

Magee, TV ^{[1
]}

Jung, DK ^{[1
]}

Isaacs, RCA ^{[1
]}

Bornmann, WG ^{[1
]}

Alaimo, CA ^{[1
]}

Coburn, CA ^{[1
]}

DiGrandi, MJ ^{[1
]}

机构：

[1] MEM SLOAN KETTERING CANC CTR, LAB BIOORGAN CHEM, SLOAN KETTERING INST CANC RES, NEW YORK, NY 10021 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1996年 / 118卷 / 12期

关键词：

D O I：

10.1021/ja952692a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An intramolecular Heck reaction (90 --> 91) serves as the key step in the total synthesis of the titled compounds. The synthetic route is based on utilizing the Wieland-Miescher ketone (5) as a matrix to provide the C and D rings of the targets and to provide functionality implements for joining this sector to an A ring precursor (6). Catalytically induced enantiotopic control and early emplacement of the oxetane are other features of the route.

引用

页码：2843 / 2859

页数：17

共 57 条

[1] STUDIES ON THE OXIDATION OF HYDRAZONES WITH IODINE AND WITH PHENYL-SELENENYL BROMIDE IN THE PRESENCE OF STRONG ORGANIC-BASES - AN IMPROVED PROCEDURE FOR THE SYNTHESIS OF VINYL IODIDES AND PHENYL-VINYL SELENIDES [J].

BARTON, DHR ;

BASHIARDES, G ;

FOURREY, JL .

TETRAHEDRON, 1988, 44 (01) :147-162

[2]

BERKOWITZ WF, 1987, J ORG CHEM, V52, P3745

[3]

BLOMBERG C, 1977, SYNTHESIS-STUTTGART, P18

[4] DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1353-+

[5] FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB [J].

DE MEIJERE, A ;

MEYER, FE .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) :2379-2411

[6] A HIGHLY EFFICIENT, PRACTICAL APPROACH TO NATURAL TAXOL [J].

DENIS, JN ;

GREENE, AE ;

GUENARD, D ;

GUERITTEVOEGELEIN, F ;

MANGATAL, L ;

POTIER, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5917-5919

[7] DEGRADATIVE ROUTES TO ELECTROPHILIC CD-SUBSTRUCTURES OF TAXOL [J].

DIGRANDI, MJ ;

COBURN, CA ;

ISAACS, RCA ;

DANISHEFSKY, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7728-7731

[8] SYNTHESIS OF COMPETENT NUCLEOPHILES FOR DELIVERING THE A RING OF TAXOL [J].

DIGRANDI, MJ ;

JUNG, DK ;

KROL, WJ ;

DANISHEFSKY, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) :4989-4992

[9] 1ST HEMISYNTHESIS OF A TAXANE COMPOUND WITH AN OXETANE GROUP IN POSITION 4 (20), 5 [J].

ETTOUATI, L ;

AHOND, A ;

POUPAT, C ;

POTIER, P .

TETRAHEDRON, 1991, 47 (47) :9823-9838

[10]

FARINA V, 1995, CHEM PHARM TAXOL

← 1 2 3 4 5 6 →