Design and de Novo Synthesis of 6-Aza-artemisinins

Karunakar Reddy Bonepally, Takahisa Hiruma, Haruki Mizoguchi, Kyohei Ochiai, Shun Suzuki, Hideaki Oikawa, Aki Ishiyama, Rei Hokari, Masato Iwatsuki, Kazuhiko Otoguro, Satoshi Omura, Hiroki Oguri

Research output: Contribution to journal › Article

1 Citation (Scopus)

Abstract

Development of designer natural product variants, 6-aza-artemisinins, enabled us to achieve structural modification of the hitherto unexplored cyclohexane moiety of artemisinin and concise de novo synthesis of the tetracyclic scaffold in just four steps from the modular assembly of three simple building blocks. This expeditious catalytic asymmetric synthetic approach generated lead candidates exhibiting superior in vivo antimalarial activities to artemisinin.

Original languageEnglish
Pages (from-to)4667-4671
Number of pages5
JournalOrganic Letters
Volume20
Issue number15
DOIs
Publication statusPublished - Aug 3 2018
Externally publishedYes

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Artemisinins
cyclohexane
assembly
Antimalarials
synthesis
products
Biological Products
Scaffolds
artemisinine

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Bonepally, K. R., Hiruma, T., Mizoguchi, H., Ochiai, K., Suzuki, S., Oikawa, H., ... Oguri, H. (2018). Design and de Novo Synthesis of 6-Aza-artemisinins. Organic Letters, 20(15), 4667-4671. https://doi.org/10.1021/acs.orglett.8b01987

Design and de Novo Synthesis of 6-Aza-artemisinins. / Bonepally, Karunakar Reddy; Hiruma, Takahisa; Mizoguchi, Haruki; Ochiai, Kyohei; Suzuki, Shun; Oikawa, Hideaki; Ishiyama, Aki; Hokari, Rei; Iwatsuki, Masato; Otoguro, Kazuhiko; Omura, Satoshi; Oguri, Hiroki.

In: Organic Letters, Vol. 20, No. 15, 03.08.2018, p. 4667-4671.

Research output: Contribution to journal › Article

Bonepally, KR, Hiruma, T, Mizoguchi, H, Ochiai, K, Suzuki, S, Oikawa, H, Ishiyama, A, Hokari, R, Iwatsuki, M, Otoguro, K, Omura, S & Oguri, H 2018, 'Design and de Novo Synthesis of 6-Aza-artemisinins', Organic Letters, vol. 20, no. 15, pp. 4667-4671. https://doi.org/10.1021/acs.orglett.8b01987
Bonepally KR, Hiruma T, Mizoguchi H, Ochiai K, Suzuki S, Oikawa H et al. Design and de Novo Synthesis of 6-Aza-artemisinins. Organic Letters. 2018 Aug 3;20(15):4667-4671. https://doi.org/10.1021/acs.orglett.8b01987
Bonepally, Karunakar Reddy ; Hiruma, Takahisa ; Mizoguchi, Haruki ; Ochiai, Kyohei ; Suzuki, Shun ; Oikawa, Hideaki ; Ishiyama, Aki ; Hokari, Rei ; Iwatsuki, Masato ; Otoguro, Kazuhiko ; Omura, Satoshi ; Oguri, Hiroki. / Design and de Novo Synthesis of 6-Aza-artemisinins. In: Organic Letters. 2018 ; Vol. 20, No. 15. pp. 4667-4671.
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