Selective Synthesis of (+)-Dysoline

Aaron Coffin, Joseph M Ready

Research output: Contribution to journalArticle

Abstract

Dysoline, a novel chromone alkaloid isolated from Dysoxylum binectariferum, was reported to have selective cytotoxicity for HT1080 fibrosarcoma cells (IC50 of 0.21 μM). Given the scarcity of natural material, a concise synthesis of (+)-dysoline was developed, allowing for further biological evaluation. An enantioselective nucleophile-catalyzed aldol lactonization formed the piperidine ring with control of relative and absolute stereochemistry. Construction of the C6-chromone core with complete regioselectivity was achieved using a Danheiser benzannulation.

Original languageEnglish (US)
Pages (from-to)648-651
Number of pages4
JournalOrganic Letters
Volume21
Issue number3
DOIs
StatePublished - Feb 1 2019

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Chromones
alkaloids
piperidine
nucleophiles
stereochemistry
Meliaceae
Regioselectivity
Nucleophiles
Stereochemistry
evaluation
Fibrosarcoma
rings
synthesis
Cytotoxicity
cells
Alkaloids
Inhibitory Concentration 50

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Selective Synthesis of (+)-Dysoline. / Coffin, Aaron; Ready, Joseph M.

In: Organic Letters, Vol. 21, No. 3, 01.02.2019, p. 648-651.

Research output: Contribution to journalArticle

Coffin, Aaron ; Ready, Joseph M. / Selective Synthesis of (+)-Dysoline. In: Organic Letters. 2019 ; Vol. 21, No. 3. pp. 648-651.
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