Literature DB >> 24032002

Gold (III) Chloride-Catalyzed 6-endo-trig Oxa-Michael Addition Reactions for Diastereoselective Synthesis of Fused Tetrahydropyranones.

Jennifer Ciesielski1, David Lebœuf, Harry A Stern, Alison J Frontier.   

Abstract

Alkynones were treated with boron trifluoride diethyl etherate to generate β-iodoallenolates, which underwent intramolecular aldol reactions to produce cycloalkenyl alcohols. Diastereoselective oxa-Michael ring closure could then be induced by treatment with a catalytic amount of gold(III) chloride, affording highly functionalized tetrahydropyran-containing ring systems.

Entities:  

Keywords:  cyclization; gold; oxa-Michael; tetrahydropyranone

Year:  2013        PMID： 24032002      PMCID： PMC3767299          DOI： 10.1002/adsc.201300265

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  35 in total

1.  Enantioselective synthesis of the oxadecalin core of phomactin A via a highly stereoselective Diels-Alder reaction.

Authors:  S R Chemler; U Iserloh; S J Danishefsky
Journal:  Org Lett       Date:  2001-09-20       Impact factor: 6.005

2.  Total synthesis of (+)-phomactin a using a B-alkyl Suzuki macrocyclization.

Authors:  Peter J Mohr; Randall L Halcomb
Journal:  J Am Chem Soc       Date:  2003-02-19       Impact factor: 15.419

3.  Gold catalysis.

Authors:  A Stephen K Hashmi; Graham J Hutchings
Journal:  Angew Chem Int Ed Engl       Date:  2006-12-04       Impact factor: 15.336

4.  Intramolecular hetero-Michael addition of beta-hydroxyenones for the preparation of highly substituted tetrahydropyranones.

Authors:  Maud Reiter; Hazel Turner; Véronique Gouverneur
Journal:  Chemistry       Date:  2006-09-18       Impact factor: 5.236

5.  1,2-Halogen migration in haloallenyl ketones: regiodivergent synthesis of halofurans.

Authors:  Anna W Sromek; Marina Rubina; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2005-08-03       Impact factor: 15.419

6.  Studies toward the tricyclic core of phomactin A. Synthesis of the reduced furanochroman subunit.

Authors:  P P Seth; N I Totah
Journal:  Org Lett       Date:  2000-08-10       Impact factor: 6.005

7.  A Nozaki-Hiyama-Kishi Ni(II)/Cr(II) coupling approach to the phomactins.

Authors:  B Mi; R E Maleczka
Journal:  Org Lett       Date:  2001-05-17       Impact factor: 6.005

8.  Formal total synthesis of (-)-apicularen A via transannular conjugate addition.

Authors:  Ferdows Hilli; Jonathan M White; Mark A Rizzacasa
Journal:  Org Lett       Date:  2004-04-15       Impact factor: 6.005

9.  An Au-catalyzed cyclialkylation of electron-rich arenes with epoxides to prepare 3-chromanols.

Authors:  Zhangjie Shi; Chuan He
Journal:  J Am Chem Soc       Date:  2004-05-19       Impact factor: 15.419

10.  A total synthesis of phomactin A.

Authors:  William P D Goldring; Gerald Pattenden
Journal:  Chem Commun (Camb)       Date:  2002-08-21       Impact factor: 6.222
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  1 in total

1.  Cascade cyclizations of acyclic and macrocyclic alkynones: studies toward the synthesis of phomactin A.

Authors:  Jennifer Ciesielski; Vincent Gandon; Alison J Frontier
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354
  1 in total

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