Literature DB >> 12074679

Novel [6 + 2] cycloaddition of fulvenes with alkenes: a facile synthesis of the anislactone and hirsutane framework.

Bor-Cherng Hong1, Yeong-Jou Shr, Jian-Lin Wu, Arun Kumar Gupta, Kuan-Jiuh Lin.   

Abstract

[reaction: see text] In contrast to the Diels-Alder reaction of fulvenes and various alkenes, 6-aminofulvenes react with maleic anhydride (or maleimide) to give [6 + 2] cycloaddition adducts, constituting an efficient and novel route to pentaleno[1,2-c]furan, pentaleno[1,2-c]pyrrole, and cyclopenta[a]pentalene skeleton.

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Year:  2002        PMID: 12074679     DOI: 10.1021/ol026103z

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  10 in total

1.  Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

Authors:  Kevin Hung; Matthew L Condakes; Luiz F T Novaes; Stephen J Harwood; Takahiro Morikawa; Zhi Yang; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2019-02-11       Impact factor: 15.419

2.  Diverse modes of reactivity of 6-(chloromethyl)-6-methylfulvene.

Authors:  Ihsan Erden; Scott Gronert; Gabriel Cabrera; Necdet Coskun; Marco Tapken
Journal:  European J Org Chem       Date:  2017-05-26

3.  Switchable regioselectivity in amine-catalysed asymmetric cycloadditions.

Authors:  Zhi Zhou; Zhou-Xiang Wang; Yuan-Chun Zhou; Wei Xiao; Qin Ouyang; Wei Du; Ying-Chun Chen
Journal:  Nat Chem       Date:  2017-01-16       Impact factor: 24.427

4.  Contemporary Synthetic Strategies toward seco-Prezizaane Sesquiterpenes from Illicium Species.

Authors:  Matthew L Condakes; Luiz F T Novaes; Thomas J Maimone
Journal:  J Org Chem       Date:  2018-12-07       Impact factor: 4.354

5.  Efficient and stereoselective dimerization of pyrroloindolizine derivatives inspired by a hypothesis for the biosynthesis of complex myrmicarin alkaloids.

Authors:  Mohammad Movassaghi; Alison E Ondrus; Bin Chen
Journal:  J Org Chem       Date:  2007-11-17       Impact factor: 4.354

6.  Total synthesis and study of myrmicarin alkaloids.

Authors:  Alison E Ondrus; Mohammad Movassaghi
Journal:  Chem Commun (Camb)       Date:  2009-05-19       Impact factor: 6.222

Review 7.  Transition metal catalyzed [6 + 2] cycloadditions.

Authors:  Amit Anand; Prabhpreet Singh; Vipan Kumar; Gaurav Bhargava
Journal:  RSC Adv       Date:  2019-08-15       Impact factor: 4.036

Review 8.  Linear Triquinane Sesquiterpenoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis.

Authors:  Yi Qiu; Wen-Jian Lan; Hou-Jin Li; Liu-Ping Chen
Journal:  Molecules       Date:  2018-08-21       Impact factor: 4.411

Review 9.  An overview of the cycloaddition chemistry of fulvenes and emerging applications.

Authors:  Ellen Swan; Kirsten Platts; Anton Blencowe
Journal:  Beilstein J Org Chem       Date:  2019-09-06       Impact factor: 2.883

10.  Tandem processes promoted by a hydrogen shift in 6-arylfulvenes bearing acetalic units at ortho position: a combined experimental and computational study.

Authors:  Mateo Alajarin; Marta Marin-Luna; Pilar Sanchez-Andrada; Angel Vidal
Journal:  Beilstein J Org Chem       Date:  2016-02-11       Impact factor: 2.883

  10 in total

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