Literature DB >> 19562093

Intramolecular thermal allenyne [2 + 2] cycloadditions; facile construction of the 5-6-4 ring core of sterpurene.

Timo V Ovaska1, Robert E Kyne.   

Abstract

A variety of 1-allenyl-2-propargyl-substituted cyclopentanol derivatives were found to undergo facile intramolecular microwave-assisted 2+2 alleneyne cycloaddition reactions to generate tricyclic 5-6-4 ring systems present in the sterpurenes.

Entities:  

Year:  2008        PMID： 19562093      PMCID： PMC2701690          DOI： 10.1016/j.tetlet.2007.11.042

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  12 in total

1.  Tandem anionic 5-Exo dig cyclization/Claisen rearrangement as an efficient route to fused polycyclic ring systems.

Authors:  T V Ovaska; J B Roses
Journal:  Org Lett       Date:  2000-07-27       Impact factor: 6.005

2.  First approach to the frondosin C ring system via a tandem cyclization/Claisen rearrangement sequence.

Authors:  Isamir Martínez; Philip E Alford; Timo V Ovaska
Journal:  Org Lett       Date:  2005-03-17       Impact factor: 6.005

3.  Progress toward the total synthesis of frondosin C.

Authors:  Xin Li; Robert E Kyne; Timo V Ovaska
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

4.  Highly efficient [2 + 2] intramolecular cyclizations of allenynes under microwave irradiation: construction of fused bicyclic compounds.

Authors:  Chang Ho Oh; Arun Kumar Gupta; Dai In Park; Nakjoong Kim
Journal:  Chem Commun (Camb)       Date:  2005-10-17       Impact factor: 6.222

5.  Microwave-assisted intramolecular [2 + 2] Allenic cycloaddition reaction for the rapid assembly of bicyclo[4.2.0]octa-1,6-dienes and bicyclo[5.2.0]nona-1,7-dienes.

Authors:  Kay M Brummond; Daitao Chen
Journal:  Org Lett       Date:  2005-08-04       Impact factor: 6.005

6.  Facile entry to the tetracyclic 5-7-6-3 tigliane ring system.

Authors:  T V Ovaska; S E Reisman; M A Flynn
Journal:  Org Lett       Date:  2001-01-11       Impact factor: 6.005

7.  A facile route to acyclic substituted alpha,beta-unsaturated aldehydes: the allene Claisen rearrangement

Authors: 
Journal:  Org Lett       Date:  2000-03-09       Impact factor: 6.005

8.  Regiospecific synthesis of bicyclo- and heterobicyclo-gem-difluorocyclobutenes using functionalized fluoroallenes and a novel Mo-catalyzed intramolecular [2 + 2] cycloaddition reaction.

Authors:  Qilong Shen; Gerald B Hammond
Journal:  J Am Chem Soc       Date:  2002-06-12       Impact factor: 15.419

9.  Preparation, structure, and unique thermal [2+2], [4+2], and [3+2] cycloaddition reactions of 4-vinylideneoxazolidin-2-one.

Authors:  Yoshikazu Horino; Masanari Kimura; Shuji Tanaka; Toshiya Okajima; Yoshinao Tamaru
Journal:  Chemistry       Date:  2003-06-06       Impact factor: 5.236

10.  A 4+3 cycloaddition approach to the synthesis of (+/-)-sterpurene.

Authors:  Michael Harmata; Gary J Bohnert
Journal:  Org Lett       Date:  2003-01-09       Impact factor: 6.005
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  2 in total

Review 1.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

2.  A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles.

Authors:  Kay M Brummond; Joshua M Osbourn
Journal:  Beilstein J Org Chem       Date:  2010-04-08       Impact factor: 2.883
  2 in total

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