CYANOCUPRATE-MEDIATED INTRAMOLECULAR BIARYL COUPLINGS APPLIED TO AN ELLAGITANNIN - SYNTHESIS OF (+)-O-PERMETHYLTELLIMAGRANDIN-II

被引：77

作者：

LIPSHUTZ, BH

LIU, ZP

KAYSER, F

机构：

[1] Department of Chemistry University of California, Santa Barbara

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(00)77248-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Generation of an intramolecularly tethered, nonracemic diaryl cuprate followed by its oxidation with ground state oxygen at -78 degrees leads to a biaryl precursor to an ellagitannin. Subsequent attachment of the appropriate glucose unit completes the synthesis of the title compound.

引用

页码：5567 / 5570

页数：4

共 18 条

[1] ALEXAKIS A, UNPUB TETRAHEDRON
[2] INHIBITION OF DNA TOPOISOMERASES BY SANGUIIN H-6, A CYTOTOXIC DIMERIC ELLAGITANNIN FROM SANGUISORBA-OFFICINALIS
BASTOW, KF
BORI, ID
FUKUSHIMA, Y
KASHIWADA, Y
TANAKA, T
NONAKA, G
NISHIOKA, I
LEE, KH
[J]. PLANTA MEDICA, 1993, 59 (03) : 240 - 245
[3] NATURALLY-OCCURRING INHIBITORS OF TOPOISOMERASE-I MEDIATED DNA RELAXATION
BERRY, DE
MACKENZIE, L
SHULTIS, EA
CHAN, JA
HECHT, SM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) : 420 - 422
[4] PROTON-TRANSFER STEPS IN STEGLICH ESTERIFICATION - A VERY PRACTICAL NEW METHOD FOR MACROLACTONIZATION
BODEN, EP
KECK, GE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) : 2394 - 2395
[5] IMPROVED ENANTIOSELECTIVITY IN ASYMMETRIC DIHYDROXYLATIONS OF TERMINAL OLEFINS USING PYRIMIDINE LIGANDS
CRISPINO, GA
JEONG, KS
KOLB, HC
WANG, ZM
XU, DQ
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) : 3785 - 3786
[6] ELLAGITANNIN CHEMISTRY - THE FIRST TOTAL CHEMICAL SYNTHESIS OF AN ELLAGITANNIN NATURAL PRODUCT, TELLIMAGRANDIN I
FELDMAN, KS
ENSEL, SM
MINARD, RD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) : 1742 - 1745
[7] Hemingway R.W., 1992, PLANT POLYPHENOLS SY
[8] INSOLE JM, 1990, J CHEM RES M, P2831
[9] Lipshutz B. H., 1992, ORG REACTIONS, P135, DOI [DOI 10.1002/0471264180.0R041.02, 10.1002/0471264180.or041.02]
[10] SYNTHESIS OF UNSYMMETRICAL BIARYLS VIA KINETIC HIGHER-ORDER CYANOCUPRATES - SCOPE, LIMITATIONS, AND SPECTROSCOPIC INSIGHTS
LIPSHUTZ, BH
SIEGMANN, K
GARCIA, E
KAYSER, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (20) : 9276 - 9282

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