Literature DB >> 21265529

Vinylogous addition of siloxyfurans to benzopyryliums: a concise approach to the tetrahydroxanthone natural products.

Tian Qin1, Richard P Johnson, John A Porco.   

Abstract

A concise approach to the tetrahydroxanthone natural products employing vinylogous addition of siloxyfurans to benzopyryliums and a late-stage Dieckmann cyclization has been developed. With this methodology, chiral, racemic forms of the natural products blennolides B and blennolide C have been synthesized in a maximum of four steps from a 5-hydroxychromone substrate. The regio- and diastereoselectivity of the vinylogous additions was probed using computational studies, which suggested the involvement of Diels-Alder-like transition states.

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Year:  2011        PMID: 21265529      PMCID: PMC3099260          DOI: 10.1021/ja110698n

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  29 in total

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Journal:  Magn Reson Chem       Date:  2007-09       Impact factor: 2.447

2.  Total syntheses and structural revision of alpha- and beta-diversonolic esters and total syntheses of diversonol and blennolide C.

Authors:  K C Nicolaou; Ang Li
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3.  The first total synthesis of nidulalin A, a dihydroxanthone possessing multiple bioactivities.

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Journal:  J Antibiot (Tokyo)       Date:  2009-07-03       Impact factor: 2.649

Review 4.  Chemistry and biology of mycotoxins and related fungal metabolites.

Authors:  Stefan Bräse; Arantxa Encinas; Julia Keck; Carl F Nising
Journal:  Chem Rev       Date:  2009-09       Impact factor: 60.622

5.  Bile pigments as HIV-1 protease inhibitors and their effects on HIV-1 viral maturation and infectivity in vitro.

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Journal:  Biochem J       Date:  1996-12-01       Impact factor: 3.857

6.  Ag-catalyzed diastereo- and enantioselective vinylogous Mannich reactions of alpha-ketoimine esters. Development of a method and investigation of its mechanism.

Authors:  Laura C Wieland; Erika M Vieira; Marc L Snapper; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-01-21       Impact factor: 15.419

7.  New mono- and dimeric members of the secalonic acid family: blennolides A-G isolated from the fungus Blennoria sp.

Authors:  Wen Zhang; Karsten Krohn; Ulrich Flörke; Gennaro Pescitelli; Lorenzo Di Bari; Sándor Antus; Tibor Kurtán; Joachim Rheinheimer; Siegfried Draeger; Barbara Schulz
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

8.  Antimycobacterial anthraquinone-chromanone compound and diketopiperazine alkaloid from the fungus Chaetomium globosum KMITL-N0802.

Authors:  Somdej Kanokmedhakul; Kwanjai Kanokmedhakul; Nutchanat Phonkerd; Kasem Soytong; Palangpon Kongsaeree; Apichart Suksamrarn
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9.  Isolation and structure elucidation of parnafungins, antifungal natural products that inhibit mRNA polyadenylation.

Authors:  Craig A Parish; Scott K Smith; Kathleen Calati; Deborah Zink; Kenneth Wilson; Terry Roemer; Bo Jiang; Deming Xu; Gerald Bills; Gonzalo Platas; Fernando Peláez; Maria Teresa Díez; Nancy Tsou; Arlene E McKeown; Richard G Ball; Mary Ann Powles; Lai Yeung; Paul Liberator; Guy Harris
Journal:  J Am Chem Soc       Date:  2008-05-08       Impact factor: 15.419

10.  Stereoselective synthesis of 4-dehydroxydiversonol employing enantioselective palladium-catalysed domino reactions.

Authors:  Lutz F Tietze; Dirk A Spiegl; Florian Stecker; Julia Major; Christian Raith; Christian Große
Journal:  Chemistry       Date:  2008       Impact factor: 5.020

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  9 in total

1.  Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

Authors:  Xiaowei Wu; Takayuki Iwata; Adam Scharf; Tian Qin; Kyle D Reichl; John A Porco
Journal:  J Am Chem Soc       Date:  2018-04-25       Impact factor: 15.419

2.  Total syntheses of graphisin A and sydowinin B.

Authors:  Andrew Little; John A Porco
Journal:  Org Lett       Date:  2012-05-23       Impact factor: 6.005

3.  Total syntheses of secalonic acids A and D.

Authors:  Tian Qin; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-12       Impact factor: 15.336

4.  Syntheses of Dimeric Tetrahydroxanthones with Varied Linkages: Investigation of "Shapeshifting" Properties.

Authors:  Tian Qin; Takayuki Iwata; Tanya T Ransom; John A Beutler; John A Porco
Journal:  J Am Chem Soc       Date:  2015-11-25       Impact factor: 15.419

5.  Atropselective syntheses of (-) and (+) rugulotrosin A utilizing point-to-axial chirality transfer.

Authors:  Tian Qin; Sarah L Skraba-Joiner; Zeinab G Khalil; Richard P Johnson; Robert J Capon; John A Porco
Journal:  Nat Chem       Date:  2015-02-02       Impact factor: 24.427

6.  Organocatalyzed, Photoredox Heteroarylation of 2-Trifluoroboratochromanones via C-H Functionalization.

Authors:  Jennifer K Matsui; Gary A Molander
Journal:  Org Lett       Date:  2017-02-03       Impact factor: 6.005

7.  Direct α-Arylation/Heteroarylation of 2-Trifluoroboratochromanones via Photoredox/Nickel Dual Catalysis.

Authors:  Jennifer K Matsui; Gary A Molander
Journal:  Org Lett       Date:  2017-01-12       Impact factor: 6.005

8.  Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones.

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Journal:  Chem Sci       Date:  2022-07-05       Impact factor: 9.969

Review 9.  Marine-Derived Xanthone from 2010 to 2021: Isolation, Bioactivities and Total Synthesis.

Authors:  Ana C S Veríssimo; Diana C G A Pinto; Artur M S Silva
Journal:  Mar Drugs       Date:  2022-05-25       Impact factor: 6.085

  9 in total

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