EFFICIENT INTRAMOLECULAR C-H INSERTION BY AN ALKYLIDENE CARBENE GENERATED FROM A VINYL-CHLORIDE

被引：34

作者：

TABER, DF

SAHLI, A

YU, H

MEAGLEY, RP

机构：

[1] Department of Chemistry and Biochemistry, University of Delaware, Newark

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 20期

关键词：

D O I：

10.1021/jo00125a050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It is observed that chloride 4 on exposure to sodium bis(trimethylsilyl)amide smoothly generates the cyclopentene 5, by insertion of the intermediate alkylidene carbene into the methine C-H. Chloride 4 is prepared in several steps from L-tartaric acid. On ozonolysis and subsequent aldol condensation, 5 is transformed into 1, a synthon for the A ring of taxol 2.

引用

页码：6571 / 6573

页数：3

共 53 条

[1] LEFT-HALF TAXOID BUILDING-BLOCKS FROM HAJOS-PARRISH KETONE
ARSENIYADIS, S
YASHUNSKY, DV
DEFREITAS, RP
BRONDIALVES, R
DORADO, MM
WANG, Q
POTIER, P
[J]. TETRAHEDRON LETTERS, 1994, 35 (50) : 9395 - 9398
[2] STUDIES TOWARDS THE TOTAL SYNTHESIS OF TAXOIDS SYNTHESIS OF AN A-RING BUILDING UNIT
ARSENIYADIS, S
YASHUNSKY, DV
DEFREITAS, RP
DORADO, MM
TOROMANOFF, E
POTIER, P
[J]. TETRAHEDRON LETTERS, 1993, 34 (07) : 1137 - 1140
[3] SYNTHESIS OF OPTICALLY ACTIVE CLELAND REAGENT [(-)-1,4-DITHIO-LG-THREITOL]
CARMACK, M
KELLEY, CJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (05) : 2171 - &
[4] MACROLACTONIZATION-TRANSANNULAR ALDOL CONDENSATION APPROACH TO THE TAXANE AB RING-SYSTEM
CHAI, KB
SAMPSON, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) : 6807 - 6813
[5] CORBEL B, 1985, SYNTHESIS-STUTTGART, P1048
[6] COREY EJ, 1975, TETRAHEDRON LETT, P2647
[7] CONCISE SYNTHESIS OF A TAXOL A-RING SYNTHON - FORMATION OF A 1,2-ALKYLIDENE LINKAGE VIA ACETYLENE CHEMISTRY
CRICH, D
CRICH, JZ
[J]. TETRAHEDRON LETTERS, 1994, 35 (16) : 2469 - 2472
[8] A-RING OXYGENATION STUDIES IN BRIDGEHEAD HYDROXYL-SUBSTITUTED TRANS-TRICYCLO[9.3.1.03,8]PENTADECAN-14-ONE CONGENERS OF TAXOL
ELMORE, SW
PAQUETTE, LA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) : 4963 - 4970
[9] A CONVERGENT CARBOHYDRATE APPROACH TO THE SYNTHESIS OF TAXOL .1. RING-A SUBUNIT
ERMOLENKO, MS
SHEKHARAM, T
LUKACS, G
POTIER, P
[J]. TETRAHEDRON LETTERS, 1995, 36 (14) : 2461 - 2464
[10] FISHER RH, 1974, TETRAHEDRON LETT, P1207

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