Traceless Solid-Phase Synthesis of Cyclopenta[<i>c</i>]quinolines and Cyclopenta[<i>c</i>]chromenes via Hetero [6+3] Cycloadditions of Fulvene. A Facile Approach to the 11-Heterosteroids Framework

Hong, Bor‐Cherng; Chen, Zhongyi; Chen, Wei‐Hung; Sun, Hsu-I; Lee, Gene‐Hsiang

doi:10.1002/jccs.200500028

Cited by 7 publications

(3 citation statements)

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“…The exact nature of the fulvene moiety is dependent mostly on its substituents (e.g., EWG or EDG) relative to the other reactants [6,42,45,67,103,153,230]. Maleimides (including maleic anhydride) [55,71,92,96,150,176–177 179–184 186,192,229,231], dimethyl acetylenedicarboxylate (DMAD) and p -benzoquinone [60,150,159,164,175,211] derivatives [174,183,200,229] are often used as the complementary dienophiles (Scheme 14, reaction pathways (i), (ii) and (iii), respectively), as well as mono- and disubstituted acetylene derivatives, such as methyl propiolate [229] and dibenzoylacetylene [150].…”

Section: Reviewmentioning

confidence: 99%

“…This requires the other reactant to have strong EDGs in order to function as a diene, otherwise fulvene dimerization becomes the preferred reaction, causing the formation of complex products. Examples of dienes that have previously been used include cyclic diketones ( o -benzoquinones) (Scheme 15, reaction pathways (i)) [60,89,156–158 160–165 211,215,226], o -quinone methides [87], o -xylylenes [125,153], polyhalogenated cyclopentadienes (Scheme 15, reaction pathways (ii)) and 2-azadienes [152,172].…”

Section: Reviewmentioning

confidence: 99%

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An overview of the cycloaddition chemistry of fulvenes and emerging applications

Swan¹,

Platts²,

Blencowe³

2019

Beilstein J. Org. Chem.

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The unusual electronic properties and unique reactivity of fulvenes have interested researchers for over a century. The propensity to form dipolar structures at relatively low temperatures and to participate as various components in cycloaddition reactions, often highly selectively, makes them ideal for the synthesis of complex polycyclic carbon scaffolds. As a result, fulvene cycloaddition chemistry has been employed extensively for the synthesis of natural products. More recently, fulvene cycloaddition chemistry has also found application to other areas including materials chemistry and dynamic combinatorial chemistry. This highlight article discusses the unusual properties of fulvenes and their varied cycloaddition chemistry, focussing on applications in organic and natural synthesis, dynamic combinatorial chemistry and materials chemistry, including dynamers, hydrogels and charge transfer complexes. Tables providing comprehensive directories of fulvene cycloaddition chemistry are provided, including fulvene intramolecular and intermolecular cycloadditions complete with reactant partners and their resulting cyclic adducts, which provide a useful reference source for synthetic chemists working with fulvenes and complex polycyclic scaffolds.

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Section: Reviewmentioning

confidence: 99%

Section: Reviewmentioning

confidence: 99%

An overview of the cycloaddition chemistry of fulvenes and emerging applications

Swan¹,

Platts²,

Blencowe³

2019

Beilstein J. Org. Chem.

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“…A library of cyclopenta[ c ]quinolones 1463 (X = NR 2 ) and cyclopenta[ c ]chromenes 1463 (X = O) as biologically active molecules was synthesized via hetero [6 + 3] cycloadditions of fulvene (Scheme ). PS aminomethyl resin 420 acylated with carboxylic acid (resin 1459 ) was treated with Et 3 OBF 4 in THF at 0 °C, and the subsequent addition of a solution of sodium cyclopentadienide in THF led to resin 1461 . Finally, fulvene resin 1461 underwent cycloaddition with benzoquinone and derivatives 1462 and yielded target oxatricyclic product 1463 .…”

Section: Miscellaneousmentioning

confidence: 99%

Traceless Solid-Phase Organic Synthesis

2019

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Traceless solid-phase synthesis represents an ultimate sophisticated synthetic strategy on insoluble supports. Compounds synthesized on solid supports can be released without a trace of the linker that was used to tether the intermediates during the synthesis. Thus, the target products are composed only of the components (atoms, functional groups) inherent to the target core structure. A wide variety of synthetic strategies have been developed to prepare products in a traceless manner, and this review is dedicated to all aspects of traceless solid-phase organic synthesis. Importantly, the synthesis does not need to be carried out on a linker designed for traceless synthesis; most of the synthetic approaches described herein were developed using standard, commercially available linkers (originally devised for solid-phase peptide synthesis). The type of structure prepared in a traceless fashion is not restricted. The individual synthetic approaches are divided into eight sections, each devoted to a different methodology for traceless synthesis. Each section consists of a brief outline of the synthetic strategy followed by a description of individual reported syntheses.

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Constructing Molecular Complexity and Diversity by Cycloaddition Reactions of Fulvenes

Hong

2016

Cross Conjugation

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Traceless Solid-Phase Synthesis of Cyclopenta[c]quinolines and Cyclopenta[c]chromenes via Hetero [6+3] Cycloadditions of Fulvene. A Facile Approach to the 11-Heterosteroids Framework

Cited by 7 publications

References 61 publications

An overview of the cycloaddition chemistry of fulvenes and emerging applications

An overview of the cycloaddition chemistry of fulvenes and emerging applications

Traceless Solid-Phase Organic Synthesis

Constructing Molecular Complexity and Diversity by Cycloaddition Reactions of Fulvenes

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