A practical synthesis of a hydroxylated sesquiterpene coumarin 10′R-acetoxy-11′-hydroxyumbelliprenin by regioselective dihydroxylation

Yasunao Hattori, Genki Kinami, Kenta Teruya, Kazuto Nosaka, Kazuya Kobayashi, Kenichi Akaji

Research output: Contribution to journalArticlepeer-review

Abstract

A practical synthesis of 10′R-acetoxy-11′-hydroxyumbelliprenin was achieved using regioselective Sharpless asymmetric dihydroxylation as a key reaction, in which the regioselectivity was achieved by using (DHQD) 2AQN as a ligand instead of the conventional (DHQD)2PHAL. 10′R-Acetoxy-11′-hydroxyumbelliprenin was synthesized by the coupling of a coumarin unit (umbelliferone) and sesquiterpene unit in 11% overall yield through 5 steps.

Original languageEnglish
Pages (from-to)423-428
Number of pages6
JournalHeterocycles
Volume87
Issue number2
DOIs
Publication statusPublished - 2013
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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