Cyclic oligolides via acylketene mediated lactonization: Synthesis and characterization

Shawn W E Eisenberg, Chixu Chen, Jiangyue Wu, Carlito B Lebrilla, Mark J. Kurth

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

An acylketene mediated cyclization protocol delivers a series of cyclic oligolides, the largest characterized cyclic oligolide having a 77-membered ring. 6-(ω-Hydroxyalkyl)dioxinone analogs were prepared and cyclizations were conducted under a variety of conditions in refluxing toluene. 1H-NMR, 13C-NMR, and several different mass spectrometric techniques were employed to verify the cyclic nature of these oligolides.

Original languageEnglish (US)
Pages (from-to)7683-7686
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number43
DOIs
StatePublished - Oct 21 1996

Fingerprint

Cyclization
Nuclear magnetic resonance
Toluene
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Eisenberg, S. W. E., Chen, C., Wu, J., Lebrilla, C. B., & Kurth, M. J. (1996). Cyclic oligolides via acylketene mediated lactonization: Synthesis and characterization. Tetrahedron Letters, 37(43), 7683-7686. https://doi.org/10.1016/0040-4039(96)01757-1

Cyclic oligolides via acylketene mediated lactonization : Synthesis and characterization. / Eisenberg, Shawn W E; Chen, Chixu; Wu, Jiangyue; Lebrilla, Carlito B; Kurth, Mark J.

In: Tetrahedron Letters, Vol. 37, No. 43, 21.10.1996, p. 7683-7686.

Research output: Contribution to journalArticle

Eisenberg, SWE, Chen, C, Wu, J, Lebrilla, CB & Kurth, MJ 1996, 'Cyclic oligolides via acylketene mediated lactonization: Synthesis and characterization', Tetrahedron Letters, vol. 37, no. 43, pp. 7683-7686. https://doi.org/10.1016/0040-4039(96)01757-1
Eisenberg, Shawn W E ; Chen, Chixu ; Wu, Jiangyue ; Lebrilla, Carlito B ; Kurth, Mark J. / Cyclic oligolides via acylketene mediated lactonization : Synthesis and characterization. In: Tetrahedron Letters. 1996 ; Vol. 37, No. 43. pp. 7683-7686.
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