168649-91-0Relevant academic research and scientific papers
Stereospecificity in [2 + 2] cycloaddition of benzyne and ketene silyl acetal
Hosoya, Takamitsu,Hasegawa, Takayuki,Kuriyama, Yokusu,Suzuki, Keisuke
, p. 3377 - 3380 (1995)
The first observation of the stereospecificity in the benzyne-olefin [2 + 2] cycloaddition is described. The key points reside in (1) the efficient method for generating benzyne species by the halogen-lithium exchange reaction of ortho-halo aryl triflates
Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction
Ambler, Brett R.,Turnbull, Ben W. H.,Suravarapu, Sankar Rao,Uteuliyev, Maulen M.,Huynh, Nancy O.,Krische, Michael J.
supporting information, p. 9091 - 9094 (2018/08/03)
The first enantioselective intermolecular metal-catalyzed cycloadditions of benzocyclobutenones via C-C bond oxidative addition are described. In the presence of a ruthenium(0) complex modified by (R)-DM-SEGPHOS, tetralone-derived ketols and benzocyclobutenones combine to form cycloadducts with complete regio- and diastereoselectivity and high enantioselectivity. Using this method, the "bay region" substructure of the angucycline natural product arenimycin was prepared.
Total synthesis and structure revision of deacetylravidomycin M
Ben, Akimi,Hsu, Day-Shin,Matsumoto, Takashi,Suzuki, Keisuke
scheme or table, p. 6460 - 6468 (2011/09/30)
Total synthesis of the unnatural enantiomer of deacetylravidomycin M was accomplished. The key steps include, (1) aryl C-glycosidation of the azido-bearing fucosyl acetate 2 by using catalytic Sc(OTf)3, (2) the [2+2] cycloaddition reaction of alkoxybenzyne bearing an azido sugar to ketene silyl acetal, and (3) the ring expansion reaction of alkoxybenzocyclobutenone. The synthesis revealed that the natural product is not the proposed amine, but the corresponding N-oxide.
Concise three-component synthesis of defucogilvocarcin M
Takemura, Isao,Imura, Koreaki,Matsumoto, Takashi,Suzuki, Keisuke
, p. 2503 - 2505 (2007/10/03)
(Matrix Presented) Concise synthesis of defucogilvocarcin M was achieved via the [2 + 2 + 2] approach to β-phenylnaphthalene structure.
Facile access to versatile polyaromatic building blocks: Selectively protected benzocyclobutenedione derivatives via regioselective [2 + 2] cycloaddition of α-alkoxybenzyne and ketene silyl acetal
Hamura, Toshiyuki,Hosoya, Takamitsu,Yamaguchi, Hiroki,Kuriyama, Yokusu,Tanabe, Mitsujiro,Miyamoto, Makoto,Yasui, Yoshizumi,Matsumoto, Takashi,Suzuki, Keisuke
, p. 3589 - 3604 (2007/10/03)
A facile, divergent access to highly oxygenated benzocyclobutene derivatives was developed via the regioselective [2 + 2] cycloaddition of α-alkoxybenzynes and ketene silyl acetals. The cycloadducts could be converted to selectively protected alkoxybenzocyclobutenediones, an attractive class of compounds for the synthesis of polyaromatic compounds. As one possible application, divergent access to a regioisomer pair of sulfonylphthalides for the Hauser approach to polyaromatic compounds is described.
