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

[21] SYNTHESIS OF AN ENANTIOMERICALLY PURE INTERMEDIATE CONTAINING THE CD SUBSTRUCTURE OF TAXOL
ISAACS, RCA
DIGRANDI, MJ
DANISHEFSKY, SJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) : 3938 - 3941
[22] SYNTHESIS OF A TAXANE TRIENE
KENDE, AS
JOHNSON, S
SANFILIPPO, P
HODGES, JC
JUNGHEIM, LN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) : 3513 - 3515
[23] KINGSTON DGI, 1993, PROGR CHEM ORGANIC N, V61
[24] SYNTHETIC STUDIES TOWARD THE TAXANE CLASS OF NATURAL-PRODUCTS
KRESS, MH
RUEL, R
MILLER, WH
KISHI, Y
[J]. TETRAHEDRON LETTERS, 1993, 34 (38) : 5999 - 6002
[25] SYNTHESIS AND REACTIONS OF (-)-CARENONE AND (+)-CARENONE
MAAS, DD
BLAGG, M
WIEMER, DF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (05) : 853 - 856
[26] A STRAIGHTFORWARD ROUTE TO FUNCTIONALIZED INTERMEDIATES CONTAINING THE CD SUBSTRUCTURE OF TAXOL
MAGEE, TV
BORNMANN, WG
ISAACS, RCA
DANISHEFSKY, SJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) : 3274 - 3276
[27] APPLICATION OF THE VICINAL OXYAMINATION REACTION WITH ASYMMETRIC INDUCTION TO THE HEMISYNTHESIS OF TAXOL AND ANALOGS
MANGATAL, L
ADELINE, MT
GUENARD, D
GUERITTEVOEGELEIN, F
POTIER, P
[J]. TETRAHEDRON, 1989, 45 (13) : 4177 - 4190
[28] A CONCISE SYNTHESIS OF A HIGHLY FUNCTIONALIZED C-ARYL TAXOL ANALOG BY AN INTRAMOLECULAR HECK OLEFINATION REACTION
MASTERS, JJ
JUNG, DK
BORNMANN, WG
DANISHEFSKY, SJ
DEGALA, S
[J]. TETRAHEDRON LETTERS, 1993, 34 (45) : 7253 - 7256
[29] A TOTAL SYNTHESIS OF TAXOL
MASTERS, JJ
LINK, JT
SNYDER, LB
YOUNG, WB
DANISHEFSKY, SJ
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (16): : 1723 - 1726
[30] A NOVEL INTRAMOLECULAR HECK REACTION - SYNTHESIS OF A CHOLESTEROL BACCATIN-III HYBRID
MASTERS, JJ
JUNG, DK
DANISHEFSKY, SJ
SNYDER, LB
PARK, TK
ISAACS, RCA
ALAIMO, CA
YOUNG, WB
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (04): : 452 - 455

← 1 2 3 4 5 6 →