A Hg(OTf)2 catalyzed intramolecular arene 1,4-addition reaction of N-benzyl donor-acceptor cyclopropenecarboxamides was developed to synthesize a series of [3.2.2]nonatriene derivatives. This novel reaction is also observed with silver(I) catalysts known to form metal carbene intermediates in competition with the Buchner reaction.
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http://dx.doi.org/10.1021/acs.orglett.5b02129 | DOI Listing |
Chem Asian J
July 2021
Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka, 558-8585, Japan.
Histrionicotoxin (HTX) alkaloids isolated from the poison arrow frogs possess a unique structure characterized by a 1-azaspiro[5.5]undecane skeleton common to the HTX family. The unique molecular architecture of HTXs and the interest as potential target drugs have prompted synthetic chemists to promote the total synthesis so far.
View Article and Find Full Text PDFChemistry
July 2017
Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka, 558-8585, Japan.
The enantioselective total syntheses of lepadiformine marine alkaloids, azatricyclic natural products isolated from marine tunicates, were completed. These alkaloids have a unique chemical structure characterized by the trans-1-azadecalin (AB ring system) fused with the spirocyclic ring (AC ring system). Here we found that a cycloisomerization reaction from functionalized linear substrates to a 1-azaspiro[4.
View Article and Find Full Text PDFOrg Biomol Chem
June 2016
Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P. R. China.
A chiral complex derived from (S)-difluorophos and Hg(OTf)2 is identified as a powerful catalyst for the Sakurai-Hosomi reaction of isatins with allyltrimethylsilane, allowing the facile synthesis of valuable building blocks 3-allyl-3-hydroxyoxindoles in up to 97% ee, with only 0.5-1.0 mol% of catalyst loading.
View Article and Find Full Text PDFOrg Lett
December 2015
Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan.
A cytotoxic marine alkaloid (-)-lepadiformine A (1) possesses a unique structure characterized by the trans-1-azadecalin AB ring system fused with the AC spiro-cyclic ring. In this research, we found that a cycloisomerization reaction from amino ynone 2 to a 1-azaspiro[4.5]decane skeleton 3, corresponding to the AC ring system of 1, is promoted by Hg(OTf)(2).
View Article and Find Full Text PDFOrg Lett
September 2015
Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States.
A Hg(OTf)2 catalyzed intramolecular arene 1,4-addition reaction of N-benzyl donor-acceptor cyclopropenecarboxamides was developed to synthesize a series of [3.2.2]nonatriene derivatives.
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