Literature DB >> 12967307

Unique strategy for the assembly of the carbon skeleton of guanacastepene A using an allenic Pauson-Khand-type reaction.

Kay M Brummond1, Dong Gao.   

Abstract

[reaction: see text] An approach to the highly functionalized tricyclic core of guanacastepene A has been developed using a rhodium(I)-catalyzed allenic Pauson-Khand reaction. This approach constitutes a conceptually novel strategy for the synthesis of this tricyclic framework, whereby the six-membered ring is formed intially followed by simultaneous formation of the five- and seven-membered rings.

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Year:  2003        PMID: 12967307     DOI: 10.1021/ol035322x

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


  7 in total

1.  An allenic Pauson-Khand approach to 6,12-guaianolides.

Authors:  Francois Grillet; Chaofeng Huang; Kay M Brummond
Journal:  Org Lett       Date:  2011-11-09       Impact factor: 6.005

2.  Computational Insight Concerning Catalytic Decision Points of the Transition Metal Catalyzed [2 + 2 + 1] Cyclocarbonylation Reaction of Allenes.

Authors:  Alexander S Bayden; Kay M Brummond; Kenneth D Jordan
Journal:  Organometallics       Date:  2006-10-23       Impact factor: 3.876

3.  Rh(I)-catalyzed Pauson-Khand-type cycloaddition reaction of ene-vinylidenecyclopropanes with carbon monoxide (CO).

Authors:  Wei Yuan; Xiang Dong; Min Shi; Patrick McDowell; Guigen Li
Journal:  Org Lett       Date:  2012-10-25       Impact factor: 6.005

4.  Asymmetric [4 + 3] cycloadditions between vinylcarbenoids and dienes: application to the total synthesis of the natural product (-)-5-epi-vibsanin E.

Authors:  Brett D Schwartz; Justin R Denton; Yajing Lian; Huw M L Davies; Craig M Williams
Journal:  J Am Chem Soc       Date:  2009-06-17       Impact factor: 15.419

5.  Five New Guanacastane-Type Diterpenes from Cultures of the Fungus Psathyrella candolleana.

Authors:  Xia Yin; Tao Feng; Zheng-Hui Li; Ying Leng; Ji-Kai Liu
Journal:  Nat Prod Bioprospect       Date:  2014-05-08

Review 6.  Application of Pauson-Khand reaction in the total synthesis of terpenes.

Authors:  Majid M Heravi; Leila Mohammadi
Journal:  RSC Adv       Date:  2021-11-29       Impact factor: 4.036

Review 7.  Diterpenes Specially Produced by Fungi: Structures, Biological Activities, and Biosynthesis (2010-2020).

Authors:  Fa-Lei Zhang; Tao Feng
Journal:  J Fungi (Basel)       Date:  2022-02-28
  7 in total

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