Toward the Synthesis of Yuzurimine-Type Alkaloids: Stereoselective Construction of the Heterocyclic Portions of Deoxyyuzurimine and Macrodaphnine

Ichiro Hayakawa, Ryosuke Nagatani, Masaki Ikeda, Dong Eun Yoo, Keita Saito, Hideo Kigoshi, Akira Sakakura

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The heterocyclic portions of yuzurimine-type alkaloids, such as deoxyyuzurimine and macrodaphnine, were synthesized by using a stereoselective hydroboration-oxidation reaction to install the C20 methyl group, the intramolecular Mitsunobu reaction to construct the E-ring portion, and the intramolecular SN2 reaction to construct the F-ring portion as key steps.

Original languageEnglish
Pages (from-to)6337-6341
Number of pages5
JournalOrganic Letters
Volume21
Issue number16
DOIs
Publication statusPublished - Aug 16 2019

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alkaloids
Alkaloids
Oxidation
synthesis
hydroboration
rings
oxidation

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Toward the Synthesis of Yuzurimine-Type Alkaloids : Stereoselective Construction of the Heterocyclic Portions of Deoxyyuzurimine and Macrodaphnine. / Hayakawa, Ichiro; Nagatani, Ryosuke; Ikeda, Masaki; Yoo, Dong Eun; Saito, Keita; Kigoshi, Hideo; Sakakura, Akira.

In: Organic Letters, Vol. 21, No. 16, 16.08.2019, p. 6337-6341.

Research output: Contribution to journalArticle

Hayakawa, Ichiro ; Nagatani, Ryosuke ; Ikeda, Masaki ; Yoo, Dong Eun ; Saito, Keita ; Kigoshi, Hideo ; Sakakura, Akira. / Toward the Synthesis of Yuzurimine-Type Alkaloids : Stereoselective Construction of the Heterocyclic Portions of Deoxyyuzurimine and Macrodaphnine. In: Organic Letters. 2019 ; Vol. 21, No. 16. pp. 6337-6341.
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