- Rapid One-Pot Access to Unique 3,4-Dihydrothiopyrano[3,4-b]indol-1(9H)-imines via Bi(OTf)3-Catalysed Tandem Friedel–Crafts Alkylation/Thia-Michael Addition
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A highly efficient and atom economical one-pot annulation strategy for novel tetrahydrothiopyrano[3,4-b]indoles is presented. This protocol involves a Bi(OTf)3 catalyzed tandem Friedel–Crafts alkylation and intramolecular thia-Michael addition reactions to furnish target molecules in an efficient manner. The method works effectively on substrates with unprotected indoles and also it is successfully employed to make tetrahydrothiepino[3,4-b]indoles. The scaffolds synthesized are diverse and first of the kind. The reaction is practically simple with broad substrate scope and vast functional group compatibility.
- Dethe, Dattatraya H.,Boda, Vijay Kumar,Mandal, Anupam
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- Application of indole-3-carbinol and diindolylmethane and derivatives thereof in preparation of medicines for treating lupus erythematosus
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The invention provides an application of indole-3-carbinol and diindolylmethane and derivatives thereof in preparation of medicines for treating lupus erythematosus. The medicines of the type can enhance ability of initiatively scavenging free radicals for cells by improving expression of specific genes in the cells, which resist the free radicals, and then reduce injury of the free radicals to the cells and tissue. Simultaneously, the used small molecule medicines are easy to obtain, low in cost, stable in quality, and convenient to save and transport, and have a wide application prospect.
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Paragraph 0030
(2017/08/27)
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- Total synthesis and absolute stereochemical assignment of (-)-communesin F
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A concise asymmetric total synthesis of (-)-communesin F (~6% overall yield in the longest linear sequence of 19 steps) is described. It features an unprecedented intramolecular oxidative coupling strategy for the elaboration of the requisite spiro-fused indoline moiety. Other notable elements are the use of TBS-protected (S)-phenylglycinol as a chiral auxiliary to induce the asymmetric formation of the spiro-fused indoline part, the mesylate-mediated formation of its G ring, and the introduction of the A ring at the final stage via intramolecular Staudinger reaction. This intramolecular Staudinger reaction proceeded smoothly at 80 °C, providing an additional example illustrating that twisted amides are more reactive than simple amides. Along with the total synthesis, we were able to assign the absolute configuration of natural communesin F as 6R,7R,8R,9S,11R.
- Zuo, Zhiwei,Xie, Weiqing,Ma, Dawei
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supporting information; experimental part
p. 13226 - 13228
(2010/11/05)
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