Literature DB >> 18759435

Au(I)-catalyzed ring expanding cycloisomerizations: total synthesis of ventricosene.

Steven G Sethofer1, Steven T Staben, Olivia Y Hung, F Dean Toste.   

Abstract

The gold(I)-catalyzed cycloisomerization of enynes containing an embedded cyclopropane unit leads selectively to the formation of ring systems containing the cyclopropylmethyl cation. A subsequent Wagner-Merwein shift provides diastereomerically pure fused cyclobutanes. The utility of this methodology for the rapid assembly of polycyclic ring systems is illustrated by the total synthesis of the angular triquinane ventricosene.

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Year:  2008        PMID： 18759435      PMCID： PMC2653418          DOI： 10.1021/ol801760w

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


  43 in total

1.  Molecular diversity through gold catalysis with alkynes.

Authors:  Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal:  Chem Commun (Camb)       Date:  2006-11-09       Impact factor: 6.222

2.  Golden carousel in catalysis: the cationic gold/propargylic ester cycle.

Authors:  Andrea Correa; Nicolas Marion; Louis Fensterbank; Max Malacria; Steven P Nolan; Luigi Cavallo
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Gold-catalyzed organic reactions.

Authors:  A Stephen K Hashmi
Journal:  Chem Rev       Date:  2007-06-20       Impact factor: 60.622

4.  Transition metal chemistry of cyclopropenes and cyclopropanes.

Authors:  Michael Rubin; Marina Rubina; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2007-07       Impact factor: 60.622

5.  (Me3Si)3SiH: twenty years after its discovery as a radical-based reducing agent.

Authors:  Chryssostomos Chatgilialoglu
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

6.  Gold(I)-catalyzed stereoselective olefin cyclopropanation.

Authors:  Magnus J Johansson; David J Gorin; Steven T Staben; F Dean Toste
Journal:  J Am Chem Soc       Date:  2005-12-28       Impact factor: 15.419

7.  Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights.

Authors:  Véronique Michelet; Patrick Y Toullec; Jean-Pierre Genêt
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

8.  Tandem gold(I)-catalyzed cyclization/electrophilic cyclopropanation of vinyl allenes.

Authors:  Gilles Lemière; Vincent Gandon; Kevin Cariou; Takahide Fukuyama; Anne-Lise Dhimane; Louis Fensterbank; Max Malacria
Journal:  Org Lett       Date:  2007-04-25       Impact factor: 6.005

9.  Gold-catalyzed intramolecular redox reaction of sulfinyl alkynes: efficient generation of alpha-oxo gold carbenoids and application in insertion into R--CO bonds.

Authors:  Guotao Li; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

10.  Catalytic regioselectivity control in ring-opening cycloisomerization of methylene- or alkylidenecyclopropyl ketones.

Authors:  Shengming Ma; Lianghua Lu; Junliang Zhang
Journal:  J Am Chem Soc       Date:  2004-08-11       Impact factor: 15.419
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  20 in total

1.  Synthesis of flinderoles B and C by a gold-catalyzed allene hydroarylation().

Authors:  Rachel M Zeldin; F Dean Toste
Journal:  Chem Sci       Date:  2011-06-24       Impact factor: 9.825

2.  Gold-catalyzed diastereoselective cycloisomerization of alkylidene-cyclopropane-bearing 1,6-diynes.

Authors:  Hongchao Zheng; Laura L Adduci; Ryan J Felix; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-11       Impact factor: 15.336

3.  Gold(I)-catalyzed diastereo- and enantioselective 1,3-dipolar cycloaddition and Mannich reactions of azlactones.

Authors:  Asa D Melhado; Giovanni W Amarante; Z Jane Wang; Marco Luparia; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

4.  Gold(i)-catalyzed addition of aldehydes to cyclopropylidene bearing 6-aryl-1,5-enynes.

Authors:  Christina A Roselli; Michel R Gagné
Journal:  Org Biomol Chem       Date:  2016-11-29       Impact factor: 3.876

5.  Enantioselective cyclizations of silyloxyenynes catalyzed by cationic metal phosphine complexes.

Authors:  Jean-François Brazeau; Suyan Zhang; Ignacio Colomer; Britton K Corkey; F Dean Toste
Journal:  J Am Chem Soc       Date:  2012-01-31       Impact factor: 15.419

6.  Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

Authors:  Weiwei Zi; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-08-19       Impact factor: 15.419

7.  A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  Synlett       Date:  2010-03-01       Impact factor: 2.454

8.  Enantioselective synthesis of cyclic carbamimidates via a three-component reaction of imines, terminal alkynes, and p-toluenesulfonylisocyanate using a monophosphine gold(I) catalyst().

Authors:  Matthew J Campbell; F Dean Toste
Journal:  Chem Sci       Date:  2011-05-12       Impact factor: 9.825

9.  A gold-catalysed enantioselective Cope rearrangement of achiral 1,5-dienes.

Authors:  Ryan J Felix; Dieter Weber; Osvaldo Gutierrez; Dean J Tantillo; Michel R Gagné
Journal:  Nat Chem       Date:  2012-04-15       Impact factor: 24.427

10.  Gold(I)-catalyzed dearomative Rautenstrauch rearrangement: enantioselective access to cyclopenta[b]indoles.

Authors:  Weiwei Zi; Hongmiao Wu; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-02-24       Impact factor: 15.419
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