Soft-enolization Baker-Venkataraman Rearrangement Enabled Total Synthesis of Dirchromones and Related 2-Substituted Chromones

被引：20

作者：

St-Gelais, Alexis ^{[1
]}

Alsarraf, Jerome ^{[1
]}

Legault, Jean ^{[1
]}

Gauthier, Charles ^{[1
,2
]}

Pichette, Andre ^{[1
]}

机构：

[1] Univ Quebec Chicoutimi, Chaire Rech Agents Anticanc Origine Nat, Lab Anal & Separat Essences Vegetales LASEVE, Dept Sci Fondamentales, 555 Blvd Univ, Chicoutimi, PQ G7H 2B1, Canada

[2] Univ Quebec, INRS Inst Armand Frappier, 531 Blvd Prairies, Laval, PQ H7V 1B7, Canada

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 23期

基金：

加拿大自然科学与工程研究理事会; 加拿大健康研究院;

关键词：

PUMMERER REACTION; FACILE; SULFOXIDES; FLAVONES; POTENT;

D O I：

10.1021/acs.orglett.8b03148

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A seven-step total synthesis of the original scaffold of cytotoxic dirchromones involving an unprecedented soft-enolization Baker-Venkataraman rearrangement was designed. The methodology enabled access to naturally occurring dirchromone 1 (21% overall yield) at gram-scale, which was screened for cytotoxicity against 13 cancer cell lines. The scope of the soft-enolization Baker-Venkataraman rearrangement encompasses diversely substituted dirchromones, including flavonoids, 2-styrylchromones, and 2-phenylethylchromones.

引用

页码：7424 / 7428

页数：5

共 15 条

[1] Total synthesis of aklanonic acid and derivatives by Baker-Venkataraman rearrangement
Krohn, K
Roemer, E
Top, M
LIEBIGS ANNALEN, 1996, (02): : 271 - 277
[2] Total synthesis of rac-γ-indomycinone by Baker-Venkataraman rearrangement
Krohn, Karsten
Tran-Thien, Hoan Trang
Vitz, Juergen
Vidal, Anne
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (12) : 1905 - 1911
[3] SYNTHESIS OF SOME SUBSTITUTED 2-(2-FURYL) CHROMONES BY SIMPLIFIED BAKER-VENKATARAMAN TRANSFORMATION
RAO, AVS
RAO, NVS
CURRENT SCIENCE, 1966, 35 (06): : 149 - &
[4] A facile synthesis of 2-(2′-vinylthiophene)chromones by the modified Baker-Venkataraman transformation
Miya, MB
Ramadas, S
Krupadanam, GLD
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1998, 37 (06): : 579 - 582
[5] A FACILE SYNTHESIS OF 2-(2'-FURYLVINYL)CHROMONES BY THE MODIFIED BAKER-VENKATARAMAN TRANSFORMATION
REDDY, MS
REDDY, CR
KRUPADANAM, GLD
SRIMANNARAYANA, G
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1989, 28 (12): : 1057 - 1059
[6] A FACILE SYNTHESIS OF 2-(THIONYL-2'-VINYL) CHROMONES BY THE MODIFIED BAKER-VENKATARAMAN TRANSFORMATION
NANDAIH, S
KRUPADANAM, GLD
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 208 : 391 - ORGN
[7] Convenient Synthesis of 3-Cinnamoyl-2-styrylchromones: Reinvestigation of the Baker-Venkataraman Rearrangement
Koenigs, Pia
Neumann, Olivia
Kataeva, Olga
Schnakenburg, Gregor
Waldvogel, Siegfried R.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (33) : 6417 - 6422
[8] A convenient synthesis of 3-cinnamoyl-5-hydroxy-2-styryl-chromones by a modified Baker-Venkataraman transformation
Pinto, DCGA
Silva, AMS
Cavaleiro, JAS
HETEROCYCLIC COMMUNICATIONS, 1996, 2 (02) : 145 - 148
[9] The application of the Baker-Venkataraman rearrangement to the synthesis of benz[b]indeno[2,1-e]pyran-10,11-dione
Thasana, N
Ruchirawat, S
TETRAHEDRON LETTERS, 2002, 43 (25) : 4515 - 4517
[10] BAKER-VENKATARAMAN REARRANGEMENT OF ORTHO-AROYLOXYACETYLDIHYDROBENZOPYRANS - SYNTHESIS OF 3,4-DIHYDRO-2 2-DIMETHYL-2H-PYRANOFLAVONES
PRASAD, KJR
IYER, CSR
IYER, PR
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1983, 22 (03): : 278 - 280

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