Literature DB >> 20160942

Construction of Novel Spiroisoxazolines via Intramolecular Cyclization/Methylation.

Erick D Ellis1, Jianping Xu, Edward J Valente, Ashton T Hamme.   

Abstract

Improved yields for the syntheses of a variety of spiroisoxazolines were achieved through intramolecular cyclization/methylation reactions of functionalized 5,5-disubstituted isoxazolines in one reaction vessel. Aromatic ring containing nitrile oxides and disubstituted geminal alkenes reacted in a 1,3-dipolar fashion to afford the corresponding 5,5-isoxazoline. A comparison of the relative location of the nucleophile and electrophile on the isoxazoline and two different ester functional groups was performed in order to determine the best isoxazoline system for the intramolecular cyclization/methylation reaction.

Entities:  

Year:  2009        PMID： 20160942      PMCID： PMC2765668          DOI： 10.1016/j.tetlet.2009.07.095

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  10 in total

1.  11-Deoxyfistularin-3, a new cytotoxic metabolite from the caribbean sponge Aplysina fistularis insularis.

Authors:  R S Compagnone; R Avila; A I Suárez; O V Abrams; H R Rangel; F Arvelo; I C Piña; E Merentes
Journal:  J Nat Prod       Date:  1999-10       Impact factor: 4.050

2.  Approaches to the synthesis of some tyrosine-derived marine sponge metabolites: synthesis of verongamine and purealidin N.

Authors:  T R Boehlow; J J Harburn; C D Spilling
Journal:  J Org Chem       Date:  2001-05-04       Impact factor: 4.354

3.  Multicomponent synthesis of spiroisoxazolines.

Authors:  Mauro F A Adamo; Donato Donati; Eleanor F Duffy; Piero Sarti-Fantoni
Journal:  J Org Chem       Date:  2005-10-14       Impact factor: 4.354

4.  The structures of aplysinamisines I, II, and III; new bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina cauliformis.

Authors:  A D Rodríguez; I C Piña
Journal:  J Nat Prod       Date:  1993-06       Impact factor: 4.050

5.  Efficient synthesis of tyrosine-derived marine sponge metabolites via acylation of amines with a coumarin.

Authors:  J Jonathan Harburn; Nigam P Rath; Christopher D Spilling
Journal:  J Org Chem       Date:  2005-08-05       Impact factor: 4.354

6.  Asymmetric Oxidative Cyclization of o-Phenolic Oxime-Esters: First Synthesis of Enantiomerically Enriched Spiroisoxazoline Methyl Esters.

Authors:  Masatoshi Murakata; Masafumi Tamura; Osamu Hoshino
Journal:  J Org Chem       Date:  1997-06-27       Impact factor: 4.354

7.  Total synthesis and stereochemical assignment of the spiroisoxazoline natural product (+)-calafianin.

Authors:  Sujata Bardhan; Daniel C Schmitt; John A Porco
Journal:  Org Lett       Date:  2006-03-02       Impact factor: 6.005

8.  Synthesis of resorcinol derived spironitronates.

Authors:  Maurice A Marsini; Yaodong Huang; Ryan W Van De Water; Thomas R R Pettus
Journal:  Org Lett       Date:  2007-07-24       Impact factor: 6.005

9.  Unique structure-activity relationship for 4-isoxazolyl-1,4-dihydropyridines.

Authors:  Gerald W Zamponi; Stephanie C Stotz; Richard J Staples; Tina M Andro; Jared K Nelson; Victoria Hulubei; Alex Blumenfeld; Nicholas R Natale
Journal:  J Med Chem       Date:  2003-01-02       Impact factor: 7.446

10.  Purealidin S and purpuramine J, bromotyrosine alkaloids from the Fijian marine sponge Druinella sp.

Authors:  Jioji N Tabudravu; Marcel Jaspars
Journal:  J Nat Prod       Date:  2002-12       Impact factor: 4.050
  10 in total
  4 in total

1.  One Pot Spiropyrazoline Synthesis via Intramolecular Cyclization/Methylation.

Authors:  Sureshbabu Dadiboyena; Ashton T Hamme
Journal:  Tetrahedron Lett       Date:  2011-05-18       Impact factor: 2.415

2.  A Model Study toward the Concise Synthesis of Bromotyrosine Derived Spiroisoxazoline Natural Products and Analogous Core Structures.

Authors:  Prasanta Das; Edward J Valente; Ashton T Hamme
Journal:  European J Org Chem       Date:  2014-05-01

3.  Synthesis and Tautomerism of Spiro-Pyrazolines.

Authors:  Sureshbabu Dadiboyena; Edward J Valente; Ashton T Hamme
Journal:  Tetrahedron Lett       Date:  2014-04-02       Impact factor: 2.415

4.  Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents.

Authors:  Prasanta Das; Sarah Boone; Dipanwita Mitra; Lindsay Turner; Ritesh Tandon; Drazen Raucher; Ashton T Hamme
Journal:  RSC Adv       Date:  2020-08-17       Impact factor: 4.036
  4 in total

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