Literature DB >> 26593869

A Concise Approach to Paxilline Indole Diterpenes.

David T George1, Eric J Kuenstner1, Sergey V Pronin1.   

Abstract

A synthetic approach to paxilline indole diterpenes is described. The route to the pentacyclic core relies on a new regioselective alkenylation of ketones and a tandem radical addition-aldol reaction sequence to access vicinal quaternary stereocenters. Emindole SB, the simplest member of the family, is synthesized in 11 steps from commercially available material to demonstrate the application of this approach.

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Year:  2015        PMID： 26593869      PMCID： PMC7556741          DOI： 10.1021/jacs.5b11129

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


  47 in total

1.  Tremorgenic indole alkaloids. The total synthesis of (-)-penitrem D.

Authors:  Amos B Smith; Naoki Kanoh; Haruaki Ishiyama; Noriaki Minakawa; Jon D Rainier; Richard A Hartz; Young Shin Cho; Haifeng Cui; William H Moser
Journal:  J Am Chem Soc       Date:  2003-07-09       Impact factor: 15.419

2.  Constructing quaternary stereogenic centers using tertiary organocuprates and tertiary radicals. Total synthesis of trans-clerodane natural products.

Authors:  Daniel S Müller; Nicholas L Untiedt; André P Dieskau; Gregory L Lackner; Larry E Overman
Journal:  J Am Chem Soc       Date:  2015-01-13       Impact factor: 15.419

3.  Constructing Quaternary Carbons from N-(Acyloxy)phthalimide Precursors of Tertiary Radicals Using Visible-Light Photocatalysis.

Authors:  Gerald Pratsch; Gregory L Lackner; Larry E Overman
Journal:  J Org Chem       Date:  2015-06-01       Impact factor: 4.354

4.  Iron(III)/NaBH4-mediated additions to unactivated alkenes: synthesis of novel 20'-vinblastine analogues.

Authors:  Erick K Leggans; Timothy J Barker; Katharine K Duncan; Dale L Boger
Journal:  Org Lett       Date:  2012-02-28       Impact factor: 6.005

5.  Total synthesis of indotertine A and drimentines A, F, and G.

Authors:  Yu Sun; Ruofan Li; Wenhao Zhang; Ang Li
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-15       Impact factor: 15.336

6.  Iron-catalyzed redox radical cyclizations of 1,6-dienes and enynes.

Authors:  Tsuyoshi Taniguchi; Naoya Goto; Asami Nishibata; Hiroyuki Ishibashi
Journal:  Org Lett       Date:  2010-01-01       Impact factor: 6.005

7.  Brominated indole alkaloids from the marine tunicate Pseudodistoma arborescens.

Authors:  M Chbani; M Païs; J M Delauneux; C Debitus
Journal:  J Nat Prod       Date:  1993-01       Impact factor: 4.050

8.  Biosynthesis of nodulisporic acid A: precursor studies.

Authors:  Kevin M Byrne; Scott K Smith; John G Ondeyka
Journal:  J Am Chem Soc       Date:  2002-06-19       Impact factor: 15.419

9.  Terpendole E and its derivative inhibit STLC- and GSK-1-resistant Eg5.

Authors:  Yuka Tarui; Takumi Chinen; Yoko Nagumo; Takayuki Motoyama; Toshiaki Hayashi; Hiroshi Hirota; Makoto Muroi; Yasuyuki Ishii; Hisae Kondo; Hiroyuki Osada; Takeo Usui
Journal:  Chembiochem       Date:  2014-03-19       Impact factor: 3.164

10.  Simple, chemoselective, catalytic olefin isomerization.

Authors:  Steven W M Crossley; Francis Barabé; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2014-11-20       Impact factor: 15.419
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  17 in total

1.  The High Chemofidelity of Metal-Catalyzed Hydrogen Atom Transfer.

Authors:  Samantha A Green; Steven W M Crossley; Jeishla L M Matos; Suhelen Vásquez-Céspedes; Sophia L Shevick; Ryan A Shenvi
Journal:  Acc Chem Res       Date:  2018-11-08       Impact factor: 22.384

2.  Twelve-Step Asymmetric Synthesis of (-)-Nodulisporic Acid C.

Authors:  Nicole A Godfrey; Devon J Schatz; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2018-09-28       Impact factor: 15.419

3.  Ph(i-PrO)SiH2: An Exceptional Reductant for Metal-Catalyzed Hydrogen Atom Transfers.

Authors:  Carla Obradors; Ruben M Martinez; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2016-03-30       Impact factor: 15.419

4.  Convergent total synthesis of (+)-calcipotriol: A scalable, modular approach to vitamin D analogs.

Authors:  Jieyu Gu; Kevin X Rodriguez; Yuzuru Kanda; Shenghua Yang; Michal Ociepa; Henrik Wilke; Arteen V Abrishami; Lars Jørgensen; Tine Skak-Nielsen; Jason S Chen; Phil S Baran
Journal:  Proc Natl Acad Sci U S A       Date:  2022-04-27       Impact factor: 12.779

5.  A Catalytic Intermolecular Formal Ene Reaction between Ketone-Derived Silyl Enol Ethers and Alkynes.

Authors:  Stephen D Holmbo; Nicole A Godfrey; Joshua J Hirner; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2016-09-16       Impact factor: 15.419

6.  Divergent Total Syntheses of (-)-Pseudocopsinine and (-)-Minovincinine.

Authors:  Xianhuang Zeng; Vyom Shukla; Dale L Boger
Journal:  J Org Chem       Date:  2020-11-18       Impact factor: 4.354

7.  Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.

Authors:  Steven W M Crossley; Carla Obradors; Ruben M Martinez; Ryan A Shenvi
Journal:  Chem Rev       Date:  2016-07-27       Impact factor: 60.622

Review 8.  Total synthesis of complex terpenoids employing radical cascade processes.

Authors:  Kevin Hung; Xirui Hu; Thomas J Maimone
Journal:  Nat Prod Rep       Date:  2018-02-21       Impact factor: 13.423

9.  Stereocontrolled Radical Bicyclizations of Oxygenated Precursors Enable Short Syntheses of Oxidized Abietane Diterpenoids.

Authors:  Darius Vrubliauskas; Benjamin M Gross; Christopher D Vanderwal
Journal:  J Am Chem Soc       Date:  2021-02-08       Impact factor: 15.419

Review 10.  Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances.

Authors:  Thiago S Silva; Fernando Coelho
Journal:  Beilstein J Org Chem       Date:  2021-07-07       Impact factor: 2.883
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