Cyclic oligolides via acylketene mediated lactonization: Synthesis and characterization

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

doi:10.1016/0040-4039(96)01757-1

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 journal › Article › peer-review

5 Scopus citations

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 language	English (US)
Pages (from-to)	7683-7686
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	43
DOIs	https://doi.org/10.1016/0040-4039(96)01757-1
State	Published - Oct 21 1996

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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AU - Eisenberg, Shawn W E

AU - Chen, Chixu

AU - Wu, Jiangyue

AU - Lebrilla, Carlito B

AU - Kurth, Mark J.

PY - 1996/10/21

Y1 - 1996/10/21

N2 - 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.

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Cyclic oligolides via acylketene mediated lactonization: Synthesis and characterization

Abstract

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