Studies aimed at the total synthesis of azadirachtin. A modeled connection of C-8 and C-14 in azadirachtin

被引：39

作者：

Fukuzaki, T ^{[1
]}

Kobayashi, S ^{[1
]}

Hibi, T ^{[1
]}

Ikuma, Y ^{[1
]}

Ishihara, J ^{[1
]}

Kanoh, N ^{[1
]}

Murai, A ^{[1
]}

机构：

[1] Hokkaido Univ, Div Chem, Grad Sch Sci, Sapporo, Hokkaido 0600810, Japan

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 17期

关键词：

D O I：

10.1021/ol026260y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] Studies on the connection between the right and left segments of azadirachtin are described. The Ireland-Claisen rearrangement of Li-enolate of the modeled ester with dichlorodimethylsilane in toluene afforded the desired limonoid framework stereoselectively in good yield.

引用

页码：2877 / 2880

页数：4

共 29 条

[1] X-RAY CRYSTALLOGRAPHIC STRUCTURE DETERMINATION OF DETIGLOYLDIHYDROAZADIRACHTIN AND REASSIGNMENT OF THE STRUCTURE OF THE LIMONOID INSECT ANTIFEEDANT AZADIRACHTIN
BROUGHTON, HB
LEY, SV
SLAWIN, AMZ
WILLIAMS, DJ
MORGAN, ED
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (01) : 46 - 47
[2] New aspects of the Ireland and related Claisen rearrangements
Chai, YH
Hong, SP
Lindsay, HA
McFarland, C
McIntosh, MC
[J]. TETRAHEDRON, 2002, 58 (15) : 2905 - 2928
[3] TOBACCO MOSAIC-VIRUS ELICITOR COAT PROTEIN GENES PRODUCE A HYPERSENSITIVE PHENOTYPE IN TRANSGENIC NICOTIANA-SYLVESTRIS PLANTS
CULVER, JN
DAWSON, WO
[J]. MOLECULAR PLANT-MICROBE INTERACTIONS, 1991, 4 (05) : 458 - 463
[4] A DIASTEREOSELECTIVE SYNTHESIS OF (+/-) TRICHODIENE
GILBERT, JC
KELLY, TA
[J]. TETRAHEDRON LETTERS, 1989, 30 (32) : 4193 - 4196
[5] ENANTIOSELECTIVE SYNTHESIS OF (-)-TRICHODIENE
GILBERT, JC
SELLIAH, RD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) : 6255 - 6265
[6] Govindachari TR, 1998, J INDIAN CHEM SOC, V75, P655
[7] FREE-RADICAL METHODOLOGY FOR CARBOHYDRATE TO CARBOCYCLE TRANSFORMATIONS - AN EFFICIENT SYNTHESIS OF THE TRICYCLIC DIHYDROFURAN PORTION OF AZADIRACHTIN
HENRY, KJ
FRASERREID, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) : 5128 - 5129
[8] Ireland R. E., 1988, ALDRICHIM ACTA, V21, P59
[9] CLAISEN REARRANGEMENT OF ALLYL ESTERS
IRELAND, RE
MUELLER, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (16) : 5897 - &
[10] STEREOCHEMICAL CONTROL IN THE ESTER ENOLATE CLAISEN REARRANGEMENT .1. STEREOSELECTIVITY IN SILYL KETENE ACETAL FORMATION
IRELAND, RE
WIPF, P
ARMSTRONG, JD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) : 650 - 657

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