74724-81-5Relevant articles and documents
Synthetic Studies of the Rubellin Natural Products: Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C
Gartman, Jackson A.,Tambar, Uttam K.
, p. 11237 - 11262 (2021/08/16)
This manuscript describes our studies of the class of natural products known as the rubellins, culminating in the total synthesis of (+)-rubellin C. These anthraquinone-based natural products contain a variety of stereochemical and architectural motifs, including a 6-5-6-fused ring system, 5 stereogenic centers, and a central quaternary center. Herein, we report our development of a strategy to target the stereochemically dense core and anthraquinone nucleus, including approaches such as a bifunctional allylboron and vinyl triflate reagent, an anthraquinone benzylic metalation strategy, and a late-stage anthraquinone introduction strategy. Our studies culminate in a successful route to highly functionalized anthraquinone-based natural product scaffolds and a stereoselective total synthesis of (+)-rubellin C. These strategies and outcomes will aid in synthetic planning toward anthraquinone-based natural products of high interest.
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.
