Total Synthesis of Tri-O-methylolivin

John Harold Dodd, John E. Starrett, Steven M. Weinreb

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

Olivin (2) is the aglycon of the antitumor antibiotic olivomycin A (1). A total synthesis of 3, the trimethyl ether of olivin, has been successfully achieved by a convergent route. The key β-methoxyenone synthon 15 was prepared from 3,5-dimethoxyphenylacetic acid (4) and ketal ester 5. Condensation of 15 and methyl orsellinate dimethyl ether gave tricyclic ketone 17 which was subsequently elaborated into 3.

Original languageEnglish (US)
Pages (from-to)1811-1812
Number of pages2
JournalJournal of the American Chemical Society
Volume106
Issue number6
DOIs
StatePublished - Mar 1 1984

Fingerprint

Ethers
Antibiotics
Ketones
Ether
Condensation
Esters
Anti-Bacterial Agents
Acids
olivin
olivomycin A
methyl orsellinate
dimethyl ether

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Dodd, J. H., Starrett, J. E., & Weinreb, S. M. (1984). Total Synthesis of Tri-O-methylolivin. Journal of the American Chemical Society, 106(6), 1811-1812. https://doi.org/10.1021/ja00318a043
Dodd, John Harold ; Starrett, John E. ; Weinreb, Steven M. / Total Synthesis of Tri-O-methylolivin. In: Journal of the American Chemical Society. 1984 ; Vol. 106, No. 6. pp. 1811-1812.
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Dodd, JH, Starrett, JE & Weinreb, SM 1984, 'Total Synthesis of Tri-O-methylolivin', Journal of the American Chemical Society, vol. 106, no. 6, pp. 1811-1812. https://doi.org/10.1021/ja00318a043

Total Synthesis of Tri-O-methylolivin. / Dodd, John Harold; Starrett, John E.; Weinreb, Steven M.

In: Journal of the American Chemical Society, Vol. 106, No. 6, 01.03.1984, p. 1811-1812.

Research output: Contribution to journalArticle

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