Model studies toward the synthesis of natural indans utilizing a thallium(III)-mediated ring-contraction reaction

被引：0

作者：

Ferraz, HMC ^{[1
]}

Aguilar, AM ^{[1
]}

Silva, LF ^{[1
]}

机构：

[1] Univ Sao Paulo, Inst Quim, BR-05513970 Sao Paulo, Brazil

来源：

SYNTHESIS-STUTTGART | 2003年 / 07期

关键词：

indan; jungianol; mutisianthol; ring contraction; thallium trinitrate;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

6-Methoxy-1-tetralone was transformed in six steps into an indan derivative related to the sesquiterpenes mutisianthol and jungianol. Key steps involve a thallium(III)-promoted ring-contraction (to assemble the indan unit) and a Wittig olefination (to attach the side chain).

引用

页码：1031 / 1034

页数：4

共 14 条

[1] Synthesis of polyalkylated indoles using a thallium(III)-mediated ring-contraction reaction
Silva, Luiz F., Jr.
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SYNTHESIS-STUTTGART, 2007, (24): : 3851 - 3857
[2] Thallium trinitrate-mediated ring contraction of 1,2-dihydronaphthalenes: an approach to the synthesis of indans
Ferraz, HMC
Silva, LF
Vieira, TO
TETRAHEDRON, 2001, 57 (09) : 1709 - 1713
[3] Construction of functionalized indans by thallium(III) promoted ring contraction of 3-alkenols
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Silva, LF
TETRAHEDRON, 2001, 57 (50) : 9939 - 9949
[4] Iodine(III)-Mediated Ring-Contraction Reactions Using Halogenated and Non-halogenated Solvents
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Nishan, Umar
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Ullah, Riaz
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SYNTHESIS-STUTTGART, 2024, 56 (13): : 2084 - 2092
[5] Reaction of thallium(III) salts with homoallylic alcohols:: Ring contraction vs. dimethoxylation
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MOLECULES, 2005, 10 (11) : 1419 - 1428
[6] Ring contraction/transannular cyclization of chiral bicyclo[3.3.1]nonanediones mediated by thallium(III) nitrate
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Bagdziunas, Gintautas
Butkus, Eugenijus
TETRAHEDRON LETTERS, 2011, 52 (02) : 346 - 348
[7] Iodine(III)-Mediated Unexpected Ring-Contraction Rearrangement and Halogenated Addition Reaction to Synthesize 3-Substituted Phthalides and Isochroman-1-One Derivatives
Meng, Fanjing
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Si, Xinxin
Liu, Tao
Cao, Yang
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (04)
[8] Synthesis of cyclohexanol derivatives by zirconocene-mediated ring-contraction reactions of seven-membered cyclic enol ethers
Barluenga, Jose
Alvarez-Rodrigo, Lucia
Rodriguez, Felix
Fananas, Francisco J.
Sordo, Tomas L.
Campomanes, Pablo
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (15) : 2607 - 2609
[9] Thallium(III)-mediated ring contraction of cis-octalins:: An approach for the diastereoselective construction of the nor-bakkane skeleton
Ferraz, Helena M. C.
Vieira, Tiago O.
Silva, Luiz F., Jr.
SYNTHESIS-STUTTGART, 2006, 16 (16): : 2748 - 2752
[10] From Ring-Expansion to Ring-Contraction: Synthesis of γ-Lactones from Cyclobutanols and Relative Stability of Five- and Six-Membered Endoperoxides toward Organic Bases
Jamey, Nicolas
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SYNTHESIS-STUTTGART, 2022, 54 (12): : 2816 - 2824

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