An Interrupted Fischer Indolization Approach toward Fused Indoline-Containing Natural Products

被引：115

作者：

Boal, Ben W. ^{[1
]}

Schammel, Alex W. ^{[1
]}

Garg, Neil K. ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 15期

关键词：

FORMAL TOTAL-SYNTHESIS; ALKALOIDS; DERIVATIVES; PHYSOSTIGMINE; ROUTE; (-)-PHYSOSTIGMINE; (-)-PHYSOVENINE; AKUAMMILINE; COMMUNESINS; CHEMISTRY;

D O I：

10.1021/ol901383j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method to access the fused indoline ring system present in a multitude of bioactive molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products by way of an interrupted Fischer indolization sequence. Our studies show that the approach will likely be amenable to the synthesis of complex targets, such as the communesin natural products.

引用

页码：3458 / 3461

页数：4

共 45 条

[1] Structure-activity relationships of 2,N6,5′-substituted adenosine derivatives with potent activity at the A2B adenosine receptor
Adachi, Hayamitsu
Palaniappan, Krishnan K.
Ivanov, Andrei A.
Bergman, Nathaniel
Gao, Zhan-Guo
Jacobson, Kenneth A.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (08) : 1810 - 1827
[2] Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B
Austin, JF
Kim, SG
Sinz, CJ
Xiao, WJ
MacMillan, DWC
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5482 - 5487
[3] FURANO-IDOLINES AND PYRANO-IDOLINES - MODEL COMPOUNDS FOR INDOLE ALKALOID STUDIES
BRITTEN, AZ
BARDSLEY, WG
HILL, CM
[J]. TETRAHEDRON, 1971, 27 (22) : 5631 - &
[4] An efficient Fischer indole synthesis of avitriptan, a potent 5-HT1D receptor agonist
Brodfuehrer, PR
Chen, BC
Sattelberg, TR
Smith, PR
Reddy, JP
Stark, DR
Quinlan, SL
Reid, JG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) : 9192 - 9202
[5] A general synthesis of substituted indoles from cyclic enol ethers and enol lactones
Campos, KR
Woo, JCS
Lee, S
Tillyer, RD
[J]. ORGANIC LETTERS, 2004, 6 (01) : 79 - 82
[6] BROMO-SUBSTITUTED PHYSOSTIGMINE ALKALOIDS FROM A MARINE BRYOZOA FLUSTRA-FOLIACEA
CARLE, JS
CHRISTOPHERSEN, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (14) : 4012 - 4013
[7] Total synthesis of 5-N-acetylardeemin and amauromine:: Practical routes to potential MDR reversal agents
Depew, KM
Marsden, SP
Zatorska, D
Zatorski, A
Bornmann, WG
Danishefsky, SJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) : 11953 - 11963
[8] DESATY D, 1964, CROAT CHEM ACTA, V36, P103
[9] An expedient route to the calabar bean alkaloids (-)-physovenine and (-)-physostigmine
El-Azab, AS
Taniguchi, T
Ogasawara, K
[J]. ORGANIC LETTERS, 2000, 2 (18) : 2757 - 2759
[10] Fischer E., BER DTSCH CHEM GES, V16, P2241, DOI [DOI 10.1002/CBER.188301602141, 10.1002/cber.188301602141]

← 1 2 3 4 5 →