Synthesis of Substituted 1,2-Dihydroisoquinolines by Palladium-Catalyzed Cascade Cyclization–Coupling of Trisubstituted Allenamides with Arylboronic Acids

Autor: Masahiro Yoshida, Ryunosuke Imaji, Shinya Shiomi

Publikováno v: Molecules, Vol 29, Iss 12, p 2917 (2024)

1,2-Dihydroisoquinolines are important compounds due to their biological and medicinal activities, and numerous approaches to their synthesis have been reported. Recently, we reported a facile synthesis of trisubstituted allenamides via N-acetylation

Externí odkaz: https://doaj.org/article/38ca8147a24c46c8ac384182f1c0e26b

Asymmetric Total Synthesis and Structure Elucidation of Huperzine H

Autor: Shinya Shiomi, Kaewsri Wilailak, Wataru Soutome, Hiromitsu Takayama, Mariko Kitajima, Hayato Ishikawa

Publikováno v: The Journal of Organic Chemistry. 87:3730-3735

A first asymmetric total synthesis of huperzine H has been achieved in a 12% overall yield from commercially available (+)-pulegone. The key steps of this synthesis include a highly diastereoselective Mukaiyama-Michael addition reaction of a pyrrole

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2841e386671dcf178efd2af74694dd81
https://doi.org/10.1021/acs.joc.1c02672

A new organocatalytic desymmetrization reaction enables the enantioselective total synthesis of madangamine E

Autor: Benjamin D A Shennan, Shinya Shiomi, Darren J. Dixon, Dhananjayan Vasu, Ken Yamazaki, Ángel L. Fuentes de Arriba, Trevor A. Hamlin

Publikováno v: Journal of the American Chemical Society
Journal of the American Chemical Society, 144(3), 1407-1415. American Chemical Society
Shiomi, S, Shennan, B D A, Yamazaki, K, Fuentes De Arriba, Á L, Vasu, D, Hamlin, T A & Dixon, D J 2022, ' A New Organocatalytic Desymmetrization Reaction Enables the Enantioselective Total Synthesis of Madangamine E ', Journal of the American Chemical Society, vol. 144, no. 3, pp. 1407-1415 . https://doi.org/10.1021/jacs.1c12040

The enantioselective total synthesis of madangamine E has been completed in 30 steps, enabled by a new catalytic and highly enantioselective desymmetrizing intramolecular Michael addition reaction of a prochiral ketone to a tethered β,β’-disubsti

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::97e983e92664a19b5bc859b395f9338f
https://doi.org/10.1021/jacs.1c12040

Total syntheses and stereochemical reassignments of mollenines A and B

Autor: Hikaru Kato, Sachiko Tsukamoto, Yuhei Umeda, Hayato Ishikawa, Kohei Wada, Shinya Shiomi

Publikováno v: Bioorganic & Medicinal Chemistry Letters. 28:2766-2769

Total syntheses of prenylated pyrrolidinoindoline alkaloids, (−)-mollenines A [(−)-1′] and B (2′), were accomplished via three- and four-step sequences including a bioinspired indole prenylation reaction followed by dioxomorpholine ring forma

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::fc7df14d30d391b749a8ed619bcc942e
https://doi.org/10.1016/j.bmcl.2018.01.065

Alkaloid Synthesis Using Organocatalysts

Autor: Hayato, Ishikawa, Shinya, Shiomi

Publikováno v: The Alkaloids. Chemistry and biology. 79

This chapter covers the literature since the advent, in the 21st century, of total syntheses of alkaloids using enantio- or diastereoselective organocatalytic reactions to construct the alkaloid scaffolds. The details of these alkaloid syntheses are

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=pmid________::f034917b60998d6b7ddfce7668c83695
https://pubmed.ncbi.nlm.nih.gov/29455834