Literature DB >> 31770485

Synthesis of (-)-Mitrephorone A via a Bioinspired Late Stage C-H Oxidation of (-)-Mitrephorone B.

Lukas Anton Wein1, Klaus Wurst2, Peter Angyal3, Lara Weisheit1, Thomas Magauer1.   

Abstract

We present a bioinspired late-stage C-H oxidation of the ent-trachylobane natural product mitrephorone B to mitrephorone A. The realization of this unprecedented transformation was accomplished by either an iron-catalyzed or electrochemical oxidation and enabled access to the densely substituted oxetane in one step. Formation of mitrephorone C, which is lacking the central oxetane unit but features a keto-function at C2, was not formed under these conditions.

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Year:  2019        PMID： 31770485      PMCID： PMC6946608          DOI： 10.1021/jacs.9b11646

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


  32 in total

1.  Catalytic asymmetric vinylation of ketone enolates.

Authors:  A Chieffi; K Kamikawa; J Ahman; J M Fox; S L Buchwald
Journal:  Org Lett       Date:  2001-06-14       Impact factor: 6.005

2.  Radical stability and its role in synthesis and catalysis.

Authors:  Johnny Hioe; Hendrik Zipse
Journal:  Org Biomol Chem       Date:  2010-06-11       Impact factor: 3.876

3.  A hexacyclic ent-trachylobane diterpenoid possessing an oxetane ring from Mitrephora glabra.

Authors:  Chen Li; Dongho Lee; Tyler N Graf; Sharnelle S Phifer; Yuka Nakanishi; Jason P Burgess; Soedarsono Riswan; Fransisca M Setyowati; Achmad M Saribi; Djaja D Soejarto; Norman R Farnsworth; Joseph O Falkinham; David J Kroll; A Douglas Kinghorn; Mansukh C Wani; Nicholas H Oberlies
Journal:  Org Lett       Date:  2005-12-08       Impact factor: 6.005

Review 4.  Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry.

Authors:  James A Bull; Rosemary A Croft; Owen A Davis; Robert Doran; Kate F Morgan
Journal:  Chem Rev       Date:  2016-09-15       Impact factor: 60.622

5.  Enantiospecific Synthesis of Both Enantiomers of the Longtailed Mealybug Pheromone and Their Evaluation in a New Zealand Vineyard.

Authors:  Remya Ramesh; Vaughn Bell; Andrew M Twidle; Rajesh Gonnade; D Srinivasa Reddy
Journal:  J Org Chem       Date:  2015-07-21       Impact factor: 4.354

Review 6.  Enantioselective Access to Robinson Annulation Products and Michael Adducts as Precursors.

Authors:  Florian Gallier; Arnaud Martel; Gilles Dujardin
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-08       Impact factor: 15.336

7.  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

8.  Combined effects on selectivity in Fe-catalyzed methylene oxidation.

Authors:  Mark S Chen; M Christina White
Journal:  Science       Date:  2010-01-29       Impact factor: 47.728

9.  Anti-inflammatory diterpenoids from the root bark of Acanthopanax gracilistylus.

Authors:  Zhi-Yuan Wu; Yi-Bei Zhang; Kong-Kai Zhu; Cheng Luo; Jing-Xian Zhang; Chun-Ru Cheng; Rui-Hong Feng; Wen-Zhi Yang; Feng Zeng; Yang Wang; Ping-Ping Xu; Ji-Ling Guo; Xuan Liu; Shu-Hong Guan; De-An Guo
Journal:  J Nat Prod       Date:  2014-10-22       Impact factor: 4.050

10.  Simple, chemoselective hydrogenation with thermodynamic stereocontrol.

Authors:  Kotaro Iwasaki; Kanny K Wan; Alberto Oppedisano; Steven W M Crossley; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2014-01-15       Impact factor: 15.419
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  5 in total

1.  Total Synthesis and Late-Stage C-H Oxidations of ent-Trachylobane Natural Products.

Authors:  Lukas Anton Wein; Klaus Wurst; Thomas Magauer
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-27       Impact factor: 15.336

Review 2.  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

3.  Silane- and peroxide-free hydrogen atom transfer hydrogenation using ascorbic acid and cobalt-photoredox dual catalysis.

Authors:  Yuji Kamei; Yusuke Seino; Yuto Yamaguchi; Tatsuhiko Yoshino; Satoshi Maeda; Masahiro Kojima; Shigeki Matsunaga
Journal:  Nat Commun       Date:  2021-02-11       Impact factor: 14.919

Review 4.  Total syntheses of strained polycyclic terpenes.

Authors:  Gleb A Chesnokov; Karl Gademann
Journal:  Chem Commun (Camb)       Date:  2022-04-19       Impact factor: 6.065

5.  Total Synthesis of (-)-Mitrephorone A Enabled by Stereoselective Nitrile Oxide Cycloaddition and Tetrasubstituted Olefin Synthesis.

Authors:  Michael Schneider; Matthieu J R Richter; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2020-10-06       Impact factor: 15.419
  5 in total

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