An enyne metathesis/(4 + 2)-dimerization route to (±)-differolide

Thomas R. Hoye; Scott M. Donaldson; Tricia J. Vos

doi:10.1021/ol9905912

An enyne metathesis/(4 + 2)-dimerization route to (±)-differolide

Thomas R. Hoye, Scott M. Donaldson, Tricia J. Vos

Chemistry (Twin Cities)

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105 Scopus citations

Abstract

(equation presented) A concise total synthesis of (±)-differolide (1) has been achieved. 2-Vinylbutenolide (2) was prepared by enyne metathesis of allyl propynoate (3) usinq the Grubbs initiator 4. This reaction was examined by ¹H NMR spectroscopy, which led to the hypothesis that low concentration of ruthenium species and high concentration of enyne substrate would be advantageous. Accordingly, slow addition of 4 to solutions of enyne 3 was found to be beneficial. Spontaneous dimerization of 2 gave (±)-differolide (1) and an isomer.

Original language	English (US)
Pages (from-to)	277-279
Number of pages	3
Journal	Organic Letters
Volume	1
Issue number	2
DOIs	https://doi.org/10.1021/ol9905912
State	Published - Jul 29 1999

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title = "An enyne metathesis/(4 + 2)-dimerization route to (±)-differolide",

abstract = "(equation presented) A concise total synthesis of (±)-differolide (1) has been achieved. 2-Vinylbutenolide (2) was prepared by enyne metathesis of allyl propynoate (3) usinq the Grubbs initiator 4. This reaction was examined by 1H NMR spectroscopy, which led to the hypothesis that low concentration of ruthenium species and high concentration of enyne substrate would be advantageous. Accordingly, slow addition of 4 to solutions of enyne 3 was found to be beneficial. Spontaneous dimerization of 2 gave (±)-differolide (1) and an isomer.",

author = "Hoye, {Thomas R.} and Donaldson, {Scott M.} and Vos, {Tricia J.}",

year = "1999",

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journal = "Organic Letters",

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AU - Donaldson, Scott M.

AU - Vos, Tricia J.

PY - 1999/7/29

Y1 - 1999/7/29

N2 - (equation presented) A concise total synthesis of (±)-differolide (1) has been achieved. 2-Vinylbutenolide (2) was prepared by enyne metathesis of allyl propynoate (3) usinq the Grubbs initiator 4. This reaction was examined by 1H NMR spectroscopy, which led to the hypothesis that low concentration of ruthenium species and high concentration of enyne substrate would be advantageous. Accordingly, slow addition of 4 to solutions of enyne 3 was found to be beneficial. Spontaneous dimerization of 2 gave (±)-differolide (1) and an isomer.

AB - (equation presented) A concise total synthesis of (±)-differolide (1) has been achieved. 2-Vinylbutenolide (2) was prepared by enyne metathesis of allyl propynoate (3) usinq the Grubbs initiator 4. This reaction was examined by 1H NMR spectroscopy, which led to the hypothesis that low concentration of ruthenium species and high concentration of enyne substrate would be advantageous. Accordingly, slow addition of 4 to solutions of enyne 3 was found to be beneficial. Spontaneous dimerization of 2 gave (±)-differolide (1) and an isomer.

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An enyne metathesis/(4 + 2)-dimerization route to (±)-differolide

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