Literature DB >> 21347498

Application of Nazarov type electrocyclization to access [6,5,6] and [6,5,5] core embedded new polycycles: an easy entry to tetrahydrofluorene scaffolds related to Taiwaniaquinoids and C-nor-D homosteroids.

Ritesh Singh1, Gautam Panda.   

Abstract

An easy, efficient and concise approach to tetrahydrofluorene [6,5,6]ABC tricyclic core embedded new polycycles has been achieved under relatively mild and catalytic Nazarov type electrocyclization conditions, using 2 mol% of Sc(OTf)(3) in anhydrous DCM (dichloromethane) at room temperature, with high yields. The generality of the reaction has been illustrated by synthesizing diverse polycycles embedded with rare heterotricyclic [6,5,5]ABC skeletons.

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Year:  2011        PMID: 21347498     DOI: 10.1039/c0ob00892c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  3 in total

1.  Nazarov cyclization of 1,4-pentadien-3-ols: preparation of cyclopenta[b]indoles and spiro[indene-1,4'-quinoline]s.

Authors:  Zhiming Wang; Xingzhu Xu; Zhanshou Gu; Wei Feng; Houjun Qian; Zhengyi Li; Xiaoqiang Sun; Ohyun Kwon
Journal:  Chem Commun (Camb)       Date:  2016-02-14       Impact factor: 6.222

2.  Beyond the Divinyl Ketone: Innovations in the Generation and Nazarov Cyclization of Pentadienyl Cation Intermediates.

Authors:  William T Spencer; Tulaza Vaidya; Alison J Frontier
Journal:  European J Org Chem       Date:  2013-06-01

3.  Novel d-Annulated Pentacyclic Steroids: Regioselective Synthesis and Biological Evaluation in Breast Cancer Cells.

Authors:  Svetlana K Vorontsova; Anton V Yadykov; Alexander M Scherbakov; Mikhail E Minyaev; Igor V Zavarzin; Ekaterina I Mikhaevich; Yulia A Volkova; Valerii Z Shirinian
Journal:  Molecules       Date:  2020-07-31       Impact factor: 4.411

  3 in total

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