Preparatively Useful Method for the Synthesis of Diels-Alder Adducts between Furan and Methyl Acrylate

Kotsuki, Hiyoshizo; Asao, Kazuhiko; Ohnishi, Hiroyuki

doi:10.1246/bcsj.57.3339

Cited by 43 publications

(15 citation statements)

References 10 publications

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“…-11exen-3-01 (25) Using general procedure 2, iodide 22 (0.51 g, 2.18 mmol) was treated with rert-butyllithium (2.82 mL, 4.79 mmol) and methacrolein (0.27 mL, 3.26 mmol) to produce compound 25 (0. 7-(2-F111yI)-2-lzepte11-4-o/ (26 (E)-7-(2-F~~ryl)-3-t~1c~thj~l-2-hepte1~-4-o/ (27) Using general procedure 2, iodide 22 (1.56 g, 6.63 mmol) was treated with ter-t-butyllithium (8.58 mL, 14.58 rnmol) and tiglic aldehyde (0.96 mL, 9.94 mmol) to produce compound 27 (0.58 g, 3.00 mmol) as a clear, colourless oil in 45% yield after purification by flash chromatography (7: 1) …”

Section: -(2-(5-methylfury1))-1 -Ckloropropane (21)mentioning

confidence: 99%

The effect of Lewis acids on the intramolecular Diels–Alder reaction of the furan diene

Rogers¹,

Keay²

1992

Can. J. Chem.

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A general method is described for effecting the intramolecular Diels–Alder reaction of the furan diene in which the side arm connecting the diene to the dienophile contains four carbon atoms. The use of 1.1 equivalents of methylaluminum dichloride at −78 °C for 2–8 h shifts the Diels–Alder equilibrium towards the products and provides the oxatricyclo adducts in good to excellent yield. Catalytic quantities of methylaluminum dichloride (10 mol%) provided a higher quantity of adduct than excess Lewis acid when the enone was substituted with alkyl groups. The scope was extended to include a precursor containing a five carbon atom side arm, and two examples containing acetylenic dienophiles that were activated by a carbonyl moiety on the side arm. Precursors having a four carbon atom side arm provided only oxatricyclo adducts having the side arm syn to the oxygen bridge. The assignment of the stereochemistry of the oxatricyclo adducts is discussed in detail.

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Section: -(2-(5-methylfury1))-1 -Ckloropropane (21)mentioning

confidence: 99%

The effect of Lewis acids on the intramolecular Diels–Alder reaction of the furan diene

Rogers¹,

Keay²

1992

Can. J. Chem.

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“…4, eqn (3)). 21 A year later, Ogawa and co-workers developed an optical resolution of (AE)-7-endooxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid by the use of (R)-(+)-and (S)-(À)-a-methylbenzylamine, respectively. 22 In 1986, Koizumi et al 23 reported the first asymmetric synthesis of 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate by means of a highly diastereoselective Diels-Alder reaction employing optically active 3-(2-pyridylsulfinyl)acrylates (S)-24 or (R)-24, respectively.…”

Section: -Carbethoxy-7-oxabicyclo[221]hept-5-enementioning

confidence: 99%

Rapid formation of complexity in the total synthesis of natural products enabled by oxabicyclo[2.2.1]heptene building blocks

Schindler

Carreira

2009

Chem. Soc. Rev.

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This critical review showcases examples of rapid formation of complexity in total syntheses starting from 7-oxabicyclo[2.2.1]hept-5-ene derivatives. An overview of methods allowing synthetic access to these building blocks is provided and their application in recently developed synthetic transformations to structurally complex systems is illustrated. In addition, the facile access to a novel oxabicyclo[2.2.1]heptene derived building block is presented which significantly enlarges the possibilities of previously known chemical transformations and is highlighted in the enantioselective route to the core of the banyaside and suomilide natural products (107 references).

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“…However, preparation of this intermediate itself proved to be difficult because, while the Diels-Alder reaction of furan and acrylate derivatives is a powerful means of synthesizing this class of compound, [24,32] no method suitable for the large-scale preparation of the endo isomer has yet been described. Establishing such a route was our first goal.…”

Section: Second-generation Monomer Synthesismentioning

confidence: 99%

Chemistry of Epoxyquinols A, B, and C and Epoxytwinol A

Shoji

Hayashi

2007

Eur J Org Chem

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The asymmetric total synthesis of epoxyquinols A, B, and C and epoxytwinol A, and computational analysis of the key biomimetic oxidative dimerization procedure are described. In the first-generation synthesis, a HfCl 4 -mediated diastereoselective Diels-Alder reaction of furan with Corey's chiral auxiliary has been developed. In the second-generation synthesis, a chromatography-free preparation of an iodolactone using acryloyl chloride as the dienophile in the Diels-Alder reaction of furan and a lipase-mediated kinetic resolution of a cyclohexenol derivative have been developed. This second-generation synthesis is suitable for large-scale synthesis.

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Preparatively Useful Method for the Synthesis of Diels-Alder Adducts between Furan and Methyl Acrylate

Cited by 43 publications

References 10 publications

The effect of Lewis acids on the intramolecular Diels–Alder reaction of the furan diene

The effect of Lewis acids on the intramolecular Diels–Alder reaction of the furan diene

Rapid formation of complexity in the total synthesis of natural products enabled by oxabicyclo[2.2.1]heptene building blocks

Chemistry of Epoxyquinols A, B, and C and Epoxytwinol A

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