Synthesis of griseolic acid analogues:: Regioselective α-facial [1,2]-migration in the rhodium acetate catalyzed reaction of D-glucose derived α-diazo-β-keto ester

被引：19

作者：

Karche, NP ^{[1
]}

Jachak, SM ^{[1
]}

Dhavale, DD ^{[1
]}

机构：

[1] Univ Poona, Dept Chem, Garware Res Ctr, Pune 411007, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 11期

关键词：

D O I：

10.1021/jo026858j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper describes an efficient route for the synthesis of known and novel griseolic acid analogues 1d and le, respectively. The key intermediate dioxabicyclo derivative 6, with the required stereochemical orientation at C6, was obtained by rhodium acetate catalyzed reaction of D-glucose derived alpha-diazo-beta-keto ester 5 in a novel high-yielding methodology.

引用

页码：4531 / 4534

页数：4

共 11 条

[1] Rhodium Carbenoid Induced [1,2]-Migration in an L-Lyxo-Configured α-Diazo β-Keto Ester: Synthesis of a New Griseolic Acid Analogue
Bhujbal, Namdeo N.
Kumar, K. S. Ajish
Dhavale, Dilip D.
SYNTHESIS-STUTTGART, 2009, (14): : 2423 - 2429
[2] Rhodium(II) acetate-catalyzed reaction of 2-amino-4,5-dihydro-3-furancarbonitriles with α-diazo-β-keto esters
Yamagata, K
Akizuki, K
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JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1998, 340 (07): : 627 - 631
[3] Application of a Stereoselective Rhodium(II)-Catalyzed Oxonium Ylide Formation-[2,3]-Sigmatropic Rearrangement of an α-Diazo-β-keto Ester to the Synthesis of 2-epi-Cinatrin C1 Dimethyl Ester
Yakura, Takayuki
Ozono, Ayaka
Matsui, Katsuaki
Yamashita, Masayuki
Fujiwara, Tomoya
SYNLETT, 2013, 24 (01) : 65 - 68
[4] Lewis acid controlled regioselective 1,2 and 1,4 reaction of α,β-unsaturated carbonyl compounds with TiIV enolates derived from α-diazo,β-keto carbonyl compounds
Deng, GS
Tian, X
Qu, ZH
Wang, JB
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (15) : 2773 - +
[5] CuO-CuAl2O4 and D-glucose catalyzed synthesis of a family of excited state intramolecular proton transfer imidazo[1,2-a]pyridine analogues and their optical properties
Balijapalli, Umamahesh
Iyer, Sathiyanarayanan Kulathu
DYES AND PIGMENTS, 2015, 121 : 88 - 98
[6] ACID-CATALYZED CONVERSION OF 2-O-(2-HYDROXYPROPYL)-D-GLUCOSE DERIVATIVES INTO 1,2-O-(1-METHYL-1,2-ETHANEDIYL)-D-GLUCOSE ACETALS - STUDIES RELATED TO O-(2-HYDROXY-PROPYL)CELLULOSE
LEE, DS
PERLIN, AS
CARBOHYDRATE RESEARCH, 1984, 125 (02) : 265 - 282
[7] Highly Regioselective, Acid-Catalyzed, Three-Component Cascade Reaction for the Synthesis of 2-aminopyridine-Decorated Imidazo[1,2-a]pyridine
He, Qiu-Xing
Liang, Yao-Feng
Xu, Chang
Yao, Xiao-Kun
Cao, Hua
Yao, Hua-Gang
ACS COMBINATORIAL SCIENCE, 2019, 21 (03) : 149 - 153
[8] FORMATION, AND STEREOCHEMISTRY, OF 1,2-O-(1-METHYL-1,2-ETHANEDIYL)-D-GLUCOSE ACETALS FORMED IN THE ACID-CATALYZED HYDROLYSIS OF O-(2-HYDROXYPROPYL)CELLULOSE
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PERLIN, AS
CARBOHYDRATE RESEARCH, 1984, 126 (01) : 101 - 114
[9] 1,3-Dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: Synthesis of 2-hydroxy-1-deoxycastanospermine analogues
Karanjule, NS
Markad, SD
Sharma, T
Sabharwal, SG
Puranik, VG
Dhavale, DD
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (04): : 1356 - 1363
[10] Aminophosphine phosphinites derived from chiral 1,2-diphenyl-2-aminoethanols: Synthesis and application in rhodium-catalyzed asymmetric hydrogenation of dehydroamino acid derivatives
Lou, RL
Mi, AQ
Jiang, YZ
Qin, Y
Li, Z
Fu, FM
Chan, ASC
TETRAHEDRON, 2000, 56 (32) : 5857 - 5863

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