The synthesis of 3,4-disubstituted furan prostanoids

Ansell, M. F.; Caton, M.P.L.; North, Peter C.

doi:10.1016/s0040-4039(01)90423-x

Cited by 28 publications

(2 citation statements)

References 3 publications

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“…The present study has been restricted to bis-propargyl ether systems only as, in these cases, we have achieved a fair amount of success in inducing predominant 1,5-shift, and the results are described herein. Incidentally, the 1,5-H shift products are 3,4-disubstituted furans, which are important in organic synthesis and are also present in various biologically interesting natural products . Our method offers an alternative way to obtain these disubstituted furans in high yields.…”

Section: Introductionmentioning

confidence: 96%

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Shifting the Reactivity of Bis-propargyl Ethers from Garratt–Braverman Cyclization Mode to 1,5-H Shift Pathway To Yield 3,4-Disubstituted Furans: A Combined Experimental and Computational Study

Das

Jana

et al. 2015

J. Org. Chem.

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Aryl or vinyl substituted bis-propargyl ethers upon base treatment generally form phthalans via the Garratt-Braverman (GB) cyclization pathway. In a major departure from this usual route, several aryl/vinyl bis-propargyl ethers with one of the acetylenic arms ending up with 2-tetrahydropyranyloxy methyl or ethoxy methyl have been shown to follow the alternative intramolecular 1,5-H shift pathway upon base treatment. The reaction has led to the formation of synthetically as well as biologically important 3,4-disubstituted furan derivatives in good yields. The initially formed E isomer in solution (CDCl3) slowly isomerizes to the Z isomer, indicating greater stability of the latter. The factors affecting the interplay between the 1,5-H shift and GB rearrangement have also been evaluated, and the results are supported by DFT-based computational study.

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Section: Introductionmentioning

confidence: 96%

“…Incidentally, the 1,5-H shift products are 3,4disubstituted furans, which are important in organic synthesis 7 and are also present in various biologically interesting natural products. 8 Our method offers an alternative way to obtain these disubstituted furans in high yields.…”

Section: ■ Introductionmentioning

confidence: 99%

Shifting the Reactivity of Bis-propargyl Ethers from Garratt–Braverman Cyclization Mode to 1,5-H Shift Pathway To Yield 3,4-Disubstituted Furans: A Combined Experimental and Computational Study

Das

Jana

et al. 2015

J. Org. Chem.

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4-Phenyloxazole

Sieburth

2001

Encyclopedia of Reagents for Organic Synthesis

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The Retro–Diels–Alder Reaction PartII. Dienophiles with One or More Heteroatom

Rickborn

1998

Organic Reactions

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This review (Part II) is topically organized around the dienophile that is generated in a retro [4 + 2] reaction, and to the extent possible follows the principles adopted for Part I, which covers reactions in which both dienophile bonding centers are carbon atoms. The present chapter encompasses retro–Diels–Alder (rDA) reactions in which one or both of the dienophile reaction centers are heteroatoms. Any of the other atoms in the starting material (cycloadduct) may be carbon or heteroatom. Substituents on all positions are encompassed, and any bond order available to any oxidation state of an element is included, as is bonding to non‐nearest neighbor atoms (e.g., bicyclics). The reader is directed to Part I (Vol. 52) for general discussion of the rDA reaction, the features that affect rates and outcome, and the use of acids, bases, other catalysts, and scavengers. Certain subclassifications (e.g., processes proposed under MS conditions, polymer applications) of rDA reactions have been omitted from both sections; these topics are listed in the Introduction to Part I. Citations to over 100 reviews on various aspects of the rDA reaction are collected at the beginning of the References to Part I. Those that are especially pertinent to Part II will be repeated here, in the context of the particular dienophile under discussion. The decision to split the review of the rDA reaction into two parts was based on the volume of literature encountered, as outlined in the Introduction to Part I. Active literature searching was concluded for both Parts in April 1995, although occasional more recent references have been included.

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The synthesis of 3,4-disubstituted furan prostanoids

Cited by 28 publications

References 3 publications

Shifting the Reactivity of Bis-propargyl Ethers from Garratt–Braverman Cyclization Mode to 1,5-H Shift Pathway To Yield 3,4-Disubstituted Furans: A Combined Experimental and Computational Study

Shifting the Reactivity of Bis-propargyl Ethers from Garratt–Braverman Cyclization Mode to 1,5-H Shift Pathway To Yield 3,4-Disubstituted Furans: A Combined Experimental and Computational Study

4-Phenyloxazole

The Retro–Diels–Alder Reaction PartII. Dienophiles with One or More Heteroatom

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