HYDROBORATION OF C-ARYLGLUCALS - SYNTHESIS OF THE BETA-C-ARYLGLUCOSIDE NUCLEUS OF CHAETIACANDIN

被引：40

作者：

FRIESEN, RW

DALJEET, AK

机构：

[1] Department of Chemistry, University of Toronto, Lash Miller Chemical Laboratories, Toronto, Ont. M5S 1A1

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 43期

关键词：

D O I：

10.1016/S0040-4039(00)97006-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hydroborations of the C-arylglucals 3a-c obtained from palladium catalyzed coupling reactions, provide the corresponding β-C-arylglucosides. Depending upon the conditions chosen for the oxidative workup, either the alcohols 5a-c or the products resulting from silyl migration (4a-c) are readily obtained. The palladium catalyzed coupling-hydroboration sequence has been applied to the synthesis of the β-C-arylglucoside nucleus of chaetiacandin, an anti-yeast antibiotic of the papulacandin family. © 1990.

引用

页码：6133 / 6136

页数：4

共 12 条

[1] BROWN HC, 1974, SYNTHESIS-STUTTGART, P77
[2] CRAGG GML, 1973, ORGANOBORANES ORGANI
[3] THE PREPARATION OF C-ARYLGLYCALS - THE PALLADIUM-CATALYZED COUPLING OF 3,4,6-TRI-O-(TERT-BUTYLDIMETHYLSILYL)-1-(TRIBUTYLSTANNYL)-D-GLUCAL AND ARYL BROMIDES
FRIESEN, RW
STURINO, CF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) : 2572 - 2574
[4] FRIESEN RW, 1990, 73RD CAN CHEM C HAL
[5] Hacksell U, 1985, Prog Med Chem, V22, P1, DOI 10.1016/S0079-6468(08)70228-5
[6] FORMATION OF C-GLYCOSIDES BY POLARITY INVERSION AT THE ANOMERIC CENTER
HANESSIAN, S
MARTIN, M
DESAI, RC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (12) : 926 - 927
[7] CHAETIACANDIN, A NOVEL PAPULACANDIN .1. FERMENTATION, ISOLATION AND CHARACTERIZATION
KOMORI, T
YAMASHITA, M
TSURUMI, Y
KOHSAKA, M
[J]. JOURNAL OF ANTIBIOTICS, 1985, 38 (04) : 455 - 459
[8] CHAETIACANDIN, A NOVEL PAPULACANDIN .2. STRUCTURE DETERMINATION
KOMORI, T
ITOH, Y
[J]. JOURNAL OF ANTIBIOTICS, 1985, 38 (04) : 544 - 546
[9] A NEW SYNTHESIS OF ARYL MONO C-GLYCOSYL DERIVATIVES OF DIALDEHYDE SUGARS
KRAUS, GA
SHI, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) : 4922 - 4925
[10] NEW SYNTHETIC STRATEGIES FOR THE CONSTRUCTION OF MEDIUM-SIZE CYCLIC ETHERS - STEREOCONTROLLED SYNTHESIS OF THE BCD RING FRAMEWORK OF BREVETOXIN-A
NICOLAOU, KC
MCGARRY, DG
SOMMERS, PK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) : 3696 - 3697

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