Literature DB >> 20843036

Total synthesis of plukenetione A.

Qiang Zhang1, Branko Mitasev, Ji Qi, John A Porco.   

Abstract

We describe an alkylative dearomatization/acid-mediated adamantane annulation sequence that allows facile access to type A polyprenylated acylphloroglucinol natural products including plukenetione A. Introduction of the 2-methyl-1-propenyl moiety was achieved via stereodivergent S(N)2 and S(N)1 cyclizations of allylic alcohol substrates.

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Year:  2010        PMID： 20843036      PMCID： PMC3014579          DOI： 10.1021/ja105784s

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


  20 in total

1.  Prenylated benzophenones and xanthones from Hypericum scabrum.

Authors:  Naonobu Tanaka; Yoshihisa Takaishi; Yasuhiro Shikishima; Yuka Nakanishi; Kenneth Bastow; Kuo-Hsiung Lee; Gisho Honda; Michiho Ito; Yoshio Takeda; Olimjon K Kodzhimatov; Ozodbek Ashurmetov
Journal:  J Nat Prod       Date:  2004-11       Impact factor: 4.050

2.  Rapid access to polyprenylated phloroglucinols via alkylative dearomatization-annulation: total synthesis of (+/-)-clusianone(1).

Authors:  Ji Qi; John A Porco
Journal:  J Am Chem Soc       Date:  2007-09-29       Impact factor: 15.419

3.  Total synthesis of (+/-)-garsubellin A.

Authors:  Akiyoshi Kuramochi; Hiroyuki Usuda; Kenzo Yamatsugu; Motomu Kanai; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2005-10-19       Impact factor: 15.419

4.  Nemorosone, the major constituent of floral resins of Clusia rosea.

Authors:  O Cuesta-Rubio; H Velez-Castro; B A Frontana-Uribe; J Cardenas
Journal:  Phytochemistry       Date:  2001-05       Impact factor: 4.072

5.  Progress toward the Synthesis of garsubellin A and related phloroglucins: the direct diastereoselective synthesis of the bicyclo[3.3.1]nonane core.

Authors:  Sarah J Spessard; Brian M Stoltz
Journal:  Org Lett       Date:  2002-05-30       Impact factor: 6.005

6.  The contribution of plukenetione A to the anti-tumoral activity of Cuban propolis.

Authors:  David Díaz-Carballo; Sascha Malak; Walter Bardenheuer; Michael Freistuehler; H Peter Reusch
Journal:  Bioorg Med Chem       Date:  2008-10-11       Impact factor: 3.641

7.  Construction of the adamantane core of plukenetione-type polycyclic polyprenylated acylphloroglucinols.

Authors:  Ryukichi Takagi; Yuta Inoue; Katsuo Ohkata
Journal:  J Org Chem       Date:  2008-12-05       Impact factor: 4.354

8.  A short biomimetic approach to the fully functionalized bicyclic framework of type A acylphloroglucinols.

Authors:  Elias A Couladouros; Marianna Dakanali; Konstantinos D Demadis; Veroniki P Vidali
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005

9.  Manganese(III)-mediated transformations of phloroglucinols: a formal oxidative [4 + 2] cycloaddition leading to bicyclo[2.2.2]octadiones.

Authors:  Branko Mitasev; John A Porco
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

10.  A new synthetic approach to the polycyclic polyprenylated acylphloroglucinols.

Authors:  Roxana Ciochina; Robert B Grossman
Journal:  Org Lett       Date:  2003-11-27       Impact factor: 6.005
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  13 in total

1.  Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes.

Authors:  Mikayo Hayashi; Lauren E Brown; John A Porco
Journal:  European J Org Chem       Date:  2016-10

2.  Regiodivergent Photocyclization of Dearomatized Acylphloroglucinols: Asymmetric Syntheses of (-)-Nemorosone and (-)-6-epi-Garcimultiflorone A.

Authors:  Saishuai Wen; Jonathan H Boyce; Sunil K Kandappa; Jayaraman Sivaguru; John A Porco
Journal:  J Am Chem Soc       Date:  2019-07-02       Impact factor: 15.419

3.  Total synthesis of (±)-7-epi-nemorosone.

Authors:  Qiang Zhang; John A Porco
Journal:  Org Lett       Date:  2012-03-26       Impact factor: 6.005

Review 4.  The lipophilic bullet hits the targets: medicinal chemistry of adamantane derivatives.

Authors:  Lukas Wanka; Khalid Iqbal; Peter R Schreiner
Journal:  Chem Rev       Date:  2013-02-25       Impact factor: 60.622

5.  The total synthesis of hyperpapuanone, hyperibone L, epi-clusianone and oblongifolin A.

Authors:  Nicole Biber; Katrin Möws; Bernd Plietker
Journal:  Nat Chem       Date:  2011-10-16       Impact factor: 24.427

6.  Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.

Authors:  Zachary Powers; Adam Scharf; Andrea Cheng; Feng Yang; Martin Himmelbauer; Takaaki Mitsuhashi; Lena Barra; Yoshimasa Taniguchi; Takashi Kikuchi; Makoto Fujita; Ikuro Abe; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-25       Impact factor: 15.336

7.  Asymmetric, stereodivergent synthesis of (-)-clusianone utilizing a biomimetic cationic cyclization.

Authors:  Jonathan H Boyce; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-10       Impact factor: 15.336

8.  Synthetic Efforts Toward [3.3.1] Bridged Bicyclic Phloroglucinol Natural Products.

Authors:  Jon T Njardarson
Journal:  Tetrahedron       Date:  2011-10-07       Impact factor: 2.457

Review 9.  An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study.

Authors:  Alexander W Schuppe; Yannan Liu; Timothy R Newhouse
Journal:  Nat Prod Rep       Date:  2020-09-15       Impact factor: 13.423

10.  Synthesis and Multiplexed Activity Profiling of Synthetic Acylphloroglucinol Scaffolds.

Authors:  Jonathan H Boyce; Benjamin J Reisman; Brian O Bachmann; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-30       Impact factor: 15.336
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