Total synthesis of baccatin III and taxol

被引：398

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
BARTON, DHR
BASHIARDES, G
FOURREY, JL
[J]. 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
COREY, EJ
CHAYKOVSKY, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) : 1353 - +
[5] FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB
DE MEIJERE, A
MEYER, FE
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) : 2379 - 2411
[6] A HIGHLY EFFICIENT, PRACTICAL APPROACH TO NATURAL TAXOL
DENIS, JN
GREENE, AE
GUENARD, D
GUERITTEVOEGELEIN, F
MANGATAL, L
POTIER, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) : 5917 - 5919
[7] DEGRADATIVE ROUTES TO ELECTROPHILIC CD-SUBSTRUCTURES OF TAXOL
DIGRANDI, MJ
COBURN, CA
ISAACS, RCA
DANISHEFSKY, SJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) : 7728 - 7731
[8] SYNTHESIS OF COMPETENT NUCLEOPHILES FOR DELIVERING THE A RING OF TAXOL
DIGRANDI, MJ
JUNG, DK
KROL, WJ
DANISHEFSKY, SJ
[J]. 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
ETTOUATI, L
AHOND, A
POUPAT, C
POTIER, P
[J]. TETRAHEDRON, 1991, 47 (47) : 9823 - 9838
[10] FARINA V, 1995, CHEM PHARM TAXOL

← 1 2 3 4 5 6 →