Catalytic asymmetric aminohydroxylation provides a short taxol side-chain synthesis

被引：67

作者：

Li, GG ^{[1
]}

Sharpless, KB ^{[1
]}

机构：

[1] Scripps Res Inst, RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA

来源：

ACTA CHEMICA SCANDINAVICA | 1996年 / 50卷 / 08期

关键词：

D O I：

10.3891/acta.chem.scand.50-0649

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The p-toluenesulfonamide derivative of the C-13 side-chain of taxol was prepared on a one third mole scale in a single step from methyl cinnamate. The process employed is catalytic asymmetric aminohydroxylation (catalytic AA). In the present case, there is no work-up other than filtration of the pure product which is insoluble in the reaction mixture. The sulfonamide protecting group is removed by acidic hydrolysis.

引用

页码：649 / 651

页数：3

共 21 条

[1] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF PARASUBSTITUTED 3'-PHENYL DOCETAXEL ANALOGS
BOURZAT, JD
LAVELLE, F
COMMERCON, A
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (08) : 809 - 814
[2] BURNS CJ, 1987, UNPUB
[3] A PRACTICAL, HIGHLY ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL SIDE-CHAIN VIA ASYMMETRIC CATALYSIS
DENG, L
JACOBSEN, EN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) : 4320 - 4323
[4] AN EFFICIENT, ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL SIDE-CHAIN
DENIS, JN
GREENE, AE
SERRA, AA
LUCHE, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (01) : 46 - 50
[5] AN IMPROVED SYNTHESIS OF THE TAXOL SIDE-CHAIN AND OF RP-56976
DENIS, JN
CORREA, A
GREENE, AE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) : 1957 - 1959
[6] FUKUYAMA T, 1995, TETRAHEDRON LETT, V36, P6376
[7] PROTECTION OF AMINES BY THE PYRIDINE-2-SULFONYL GROUP AND ITS CLEAVAGE UNDER MILD CONDITIONS (SMI2 OR ELECTROLYSIS)
GOULAOUICDUBOIS, C
GUGGISBERG, A
HESSE, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) : 5969 - 5972
[8] NEW SYNTHESIS OF L-2-AMINO-3-OXALYLAMINOPROPIONIC ACID, LATHYRUS-SATIVUS NEUROTOXIN
HASKELL, BE
BOWLUS, SB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (01) : 159 - 160
[9] FIRST TOTAL SYNTHESIS OF TAXOL .1. FUNCTIONALIZATION OF THE B-RING
HOLTON, RA
SOMOZA, C
KIM, HB
LIANG, F
BIEDIGER, RJ
BOATMAN, PD
SHINDO, M
SMITH, CC
KIM, SC
NADIZADEH, H
SUZUKI, Y
TAO, CL
VU, P
TANG, SH
ZHANG, PS
MURTHI, KK
GENTILE, LN
LIU, JH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (04) : 1597 - 1598
[10] Catalytic asymmetric aminohydroxylation (AA) of olefins
Li, GG
Chang, HT
Sharpless, KB
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04): : 451 - 454

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