Literature DB >> 16599616

Synthesis and structure revision of calyxin natural products.

Xia Tian1, James J Jaber, Scott D Rychnovsky.   

Abstract

Tandem Prins cyclization and Friedel-Crafts reaction with an electron-rich aromatic ring were used to prepare the core structures of calyxin natural products. The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, were synthesized, and the structures were reassigned on the basis of NMR data and synthetic correlations.

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Year:  2006        PMID: 16599616     DOI: 10.1021/jo060094g

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  10 in total

1.  Use of a tandem Prins/Friedel-Crafts reaction in the construction of the indeno-tetrahydropyridine core of the haouamine alkaloids: formal synthesis of (-)-haouamine A.

Authors:  Erik Fenster; Charlie Fehl; Jeffrey Aubé
Journal:  Org Lett       Date:  2011-04-25       Impact factor: 6.005

2.  Racemization in Prins cyclization reactions.

Authors:  Ramesh Jasti; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2006-10-18       Impact factor: 15.419

3.  Tandem processes identified from reaction screening: nucleophilic addition to aryl N-phosphinylimines employing La(III)-TFAA activation.

Authors:  Hidenori Kinoshita; Oscar J Ingham; Winnie W Ong; Aaron B Beeler; John A Porco
Journal:  J Am Chem Soc       Date:  2010-05-12       Impact factor: 15.419

4.  Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family.

Authors:  David W Lin; Takeshi Masuda; Moritz B Biskup; Jonathan D Nelson; Phil S Baran
Journal:  J Org Chem       Date:  2011-01-20       Impact factor: 4.354

5.  Synthesis of 2,6-disubstituted dihydropyrans via an efficient BiBr(3)-initiated three component, one-pot cascade.

Authors:  Robert J Hinkle; Yajing Lian; Lee C Speight; Heather E Stevenson; Melissa M Sprachman; Lauren A Katkish; M Christa Mattern
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

6.  Synthesis and structural reassignment of (+)-epicalyxin F.

Authors:  Xia Tian; Scott D Rychnovsky
Journal:  Org Lett       Date:  2007-10-25       Impact factor: 6.005

7.  Formal synthesis of (-)-kendomycin featuring a Prins-cyclization to construct the macrocycle.

Authors:  Kevin B Bahnck; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2008-09-04       Impact factor: 15.419

8.  Preparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF.

Authors:  Otome E Okoromoba; Gerald B Hammond; Bo Xu
Journal:  Org Lett       Date:  2015-08-11       Impact factor: 6.005

9.  Evidence for pi-stacking as a source of stereocontrol in the synthesis of the core pyranochromene ring system common to calyxin I, calyxin J, and epicalyxin J.

Authors:  Sidika Polat Cakir; Sean Stokes; Andrzej Sygula; Keith T Mead
Journal:  J Org Chem       Date:  2009-10-02       Impact factor: 4.354

10.  Heat Shock Protein-Inducing Property of Diarylheptanoid Containing Chalcone Moiety from Alpinia katsumadai.

Authors:  Joo-Won Nam; Yun-Sil Lee
Journal:  Molecules       Date:  2017-10-17       Impact factor: 4.411

  10 in total

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