Synthesis of Two Unnatural Oxygenated Aaptaminoids

被引：9

作者：

Abbiati, Giorgio ^{[1
]}

Doda, Arjana ^{[1
]}

Dell'Acqua, Monica ^{[1
]}

Pirovano, Valentina ^{[1
]}

Facoetti, Diego ^{[1
]}

Rizzato, Silvia ^{[2
]}

Rossi, Elisabetta ^{[1
]}

机构：

[1] Univ Milan, Dipartimento Sci Farmaceut, Sez Chim Gen & Organ A Marchesini, I-20133 Milan, Italy

[2] Univ Milan, Dipartimento Chim, I-20133 Milan, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 22期

关键词：

MODIFIED CURTIUS REACTION; ALPHA-BLOCKING ACTIVITY; CONVENIENT REAGENT; MARINE ALKALOIDS; DERIVATIVES; CYCLIZATION; ANALOGS; 4(1H)-QUINOLONES; ISOQUINOLINES; ISOAAPTAMINE;

D O I：

10.1021/jo3020598

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two unprecedented oxygenated aaptaminoids have been synthesized starting from cheap and easily available 2,3-dihydroxybenzoic acid with the satisfactory overall yields of 31% and 34%. The key step of the procedure is the divergent thermic 5-exodig vs base-promoted 6-endodig cyclization of a 5-alkynylquinolinone derivative.

引用

页码：10461 / 10467

页数：7

共 50 条

[41] Total synthesis of natural (-)- and unnatural (+)-Melearoride A
Reed, Carson W.
Fulton, Mark G.
Nance, Kellie D.
Lindsley, Craig W.
TETRAHEDRON LETTERS, 2019, 60 (10) : 743 - 745
[42] AN ASYMMETRIC TOTAL SYNTHESIS OF UNNATURAL (+)-ANISOMYCIN
MEYERS, AI
DUPRE, B
HETEROCYCLES, 1987, 25 : 113 - 116
[43] Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives
Ghavre, Mukund
Froese, Jordan
Pour, Milan
Hudlicky, Tomas
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (19) : 5642 - 5691
[44] CANNABIS .27. SYNTHESIS OF 8-OXYGENATED, 10-OXYGENATED, AND 11-OXYGENATED CANNABINOLS
NOVAK, J
SALEMINK, CA
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (12): : 2867 - 2871
[45] MODELING THE SYNTHESIS OF AN OXYGENATED BIOFUEL ADDITIVE
Elena-Emilia, Oprescu
Emil, Stepan
Cristina, Popa
Ion, Bolocan
ENERGY AND CLEAN TECHNOLOGIES, 2015, : 337 - 344
[46] SYNTHESIS OF BENZOFURANS FROM OXYGENATED PHENOXYAMINES
CASTELLINO, AJ
RAPOPORT, H
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (23): : 4399 - 4404
[47] Synthesis of oxygenated 2-methylindolines
Chang, Meng-Yang
Chen, Yi-Chia
Chan, Chieh-Kai
TETRAHEDRON LETTERS, 2014, 55 (17) : 2876 - 2878
[48] TOTAL SYNTHESIS OF OXYGENATED LUPIN ALKALOIDS
VANTAMELEN, EE
BARAN, JS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (17) : 4659 - 4670
[49] SYNTHESIS OF 18-OXYGENATED PROGESTERONES
PAPPO, R
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (04) : 1010 - 1011
[50] Synthesis and structure of oxygenated fullerene film
Shevtsov, YV
Berdinsky, AS
Okotrub, AV
Yanovsky, YA
Ayupov, BM
Guselnikov, AV
Kravtchenko, VS
APEIE-98: 1998 4TH INTERNATIONAL CONFERENCE ON ACTUAL PROBLEMS OF ELECTRONIC INSTRUMENT ENGINEERING PROCEEDINGS, VOL 1, 1998, : 54 - 54

← 1 2 3 4 5 →