Macrocyclic lactam synthesis via a ring expansion reaction: Construction of the cripowellin skeleton

被引：20

作者：

Moon, B ^{[1
]}

Han, S

Yoon, Y

Kwon, H

机构：

[1] Sogang Univ, Dept Chem, Seoul 121742, South Korea

[2] Yonsei Univ, Ctr Bioact Mol Hybrids, Seoul 120749, South Korea

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 06期

关键词：

D O I：

10.1021/ol047520+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cripowellin ring skeleton, a macrocyclic [2.3.5]-bicyclic ketolactam, was smoothly generated via construction of a spiro(benzazepin-cyclohexane-1, 3-dione) employing oxidative cyclization as a key step and a subsequent ring expansion reaction.

引用

页码：1031 / 1034

页数：4

共 18 条

[1] A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE
ADAM, W
BIALAS, J
HADJIARAPOGLOU, L
[J]. CHEMISCHE BERICHTE, 1991, 124 (10) : 2377 - 2377
[2] Hypervalent iodine(III)-induced intramolecular cyclization of α-(aryl)alkyl-β-dicarbonyl compounds:: A convenient synthesis of benzannulated and spirobenzannulated compounds
Arisawa, M
Ramesh, NG
Nakajima, M
Tohma, H
Kita, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) : 59 - 65
[3] MANGANESE(III) ACETATE INDUCED CYCLIZATION OF ALPHA-ARYLALKYL AND ALPHA-(ARYLOXY)ALKYL BETA-DICARBONYL DERIVATIVES
CITTERIO, A
FANCELLI, D
FINZI, C
PESCE, L
SANTI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) : 2713 - 2718
[4] Gehling M., 1997, [No title captured], Patent No. [19610279, DE19610279A1]
[5] TOTAL SYNTHESIS OF (+-)-FAWCETTIMINE
HEATHCOCK, CH
BLUMENKOPF, TA
SMITH, KM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) : 1548 - 1562
[6] An oxidative intramolecular phenolic coupling reaction for the synthesis of amaryllidaceae alkaloids using a hypervalent iodine(III) reagent
Kita, Y
Takada, T
Gyoten, M
Tohma, H
Zenk, MH
Eichhorn, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) : 5857 - 5864
[7] Oxidative intramolecular phenolic coupling reaction induced by a hypervalent iodine(III) reagent: Leading to galanthamine-type amaryllidaceae alkaloids
Kita, Y
Arisawa, M
Gyoten, M
Nakajima, M
Hamada, R
Tohma, H
Takada, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) : 6625 - 6633
[8] SELECTIVE HYDRIDE-MEDIATED CONJUGATE REDUCTION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS USING [(PH3P)CUH]6
MAHONEY, WS
BRESTENSKY, DM
STRYKER, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (01) : 291 - 293
[9] SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF 2 CHIRAL (NONRACEMIC) 4-SUBSTITUTED QUINOLIZIDINES
MCINTOSH, JM
MATASSA, LC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) : 4452 - 4457
[10] MIYASHITA N, 1977, J ORG CHEM, V42, P3772

← 1 2 →