Literature DB >> 11277774

Synthesis of a 2,9-dioxabicyclo[3.3.1]nonane via double intramolecular hetero-Michael addition: entry to the F-G ring system of the azaspiracids.

J Aiguade1, J Hao, C J Forsyth.   

Abstract

[structure: see text]. An effective approach to form a 1,3-disubstituted 2,9-dioxabicyclo[3.3.1]nonane system representing the core of the F and G rings (C28-C34) of the azaspiracid natural products has been developed. The double intramolecular hetero-Michael addition (DIHMA) of a diol upon an ynone generated the bicyclic ketal in a highly diastereoselective fashion.

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Year:  2001        PMID： 11277774

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Synthesis of the ABCD and ABCDE ring systems of azaspiracid-1.

Authors:  Xiao-Ti Zhou; Rich G Carter
Journal:  Chem Commun (Camb)       Date:  2004-09-20       Impact factor: 6.222

2.  Synthesis of the southern FGHI ring system of azaspiracid-1 and investigation into the controlling elements of C28- and C36-ketalization.

Authors:  Xiao-Ti Zhou; Liang Lu; Daniel P Furkert; Charles E Wells; Rich G Carter
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-20       Impact factor: 15.336

3.  Synthesis of the C1-C26 northern portion of azaspiracid-1: kinetic versus thermodynamic control of the formation of the bis-spiroketal.

Authors:  Xiao-Ti Zhou; Rich G Carter
Journal:  Angew Chem Int Ed Engl       Date:  2006-03-03       Impact factor: 15.336

4.  Synthetic and Computational Studies on the ABC Trioxadispiroketal Subunit of the Marine Biotoxin Azaspiracid-1.

Authors:  Jialiang Li; Xiaohua Li; David R Mootoo
Journal:  Nat Prod Commun       Date:  2008-11       Impact factor: 0.986

5.  Application of a Double Aza-Michael Reaction in a 'Click, Click, Cy-Click' Strategy: From Bench to Flow.

Authors:  Qin Zang; Salim Javed; Farman Ullah; Aihua Zhou; Christopher A Knudtson; Danse Bi; Fatima Z Basha; Michael G Organ; Paul R Hanson
Journal:  Synthesis (Stuttg)       Date:  2011-09-01       Impact factor: 3.157

6.  Combined Treatment of Nitrated [6,6,6]Tricycles Derivative (SK2)/Ultraviolet C Highly Inhibits Proliferation in Oral Cancer Cells In Vitro.

Authors:  Sheng-Chieh Wang; Ching-Yu Yen; Jun-Ping Shiau; Meng-Yang Chang; Ming-Feng Hou; Jen-Yang Tang; Hsueh-Wei Chang
Journal:  Biomedicines       Date:  2022-05-22

7.  Synergistic Antiproliferation of Cisplatin and Nitrated [6,6,6]Tricycle Derivative (SK2) for a Combined Treatment of Oral Cancer Cells.

Authors:  Sheng-Chieh Wang; Ching-Yu Yen; Jun-Ping Shiau; Meng-Yang Chang; Ming-Feng Hou; Jiiang-Huei Jeng; Jen-Yang Tang; Hsueh-Wei Chang
Journal:  Antioxidants (Basel)       Date:  2022-05-08

8.  Synthesis of the ABC ring system of azaspiracid. 1. Effect of D ring truncation on bis-spirocyclization.

Authors:  Rich G Carter; T Campbell Bourland; David E Graves
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005

9.  Total synthesis of (+)-azaspiracid-1. An exhibition of the intricacies of complex molecule synthesis.

Authors:  David A Evans; Lisbet Kvaernø; Travis B Dunn; André Beauchemin; Brian Raymer; Jason A Mulder; Edward J Olhava; Martin Juhl; Katsuji Kagechika; David A Favor
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

10.  Antiproliferation- and Apoptosis-Inducible Effects of a Novel Nitrated [6,6,6]Tricycle Derivative (SK2) on Oral Cancer Cells.

Authors:  Sheng-Chieh Wang; Meng-Yang Chang; Jun-Ping Shiau; Ammad Ahmad Farooqi; Yu-Hsiang Huang; Jen-Yang Tang; Hsueh-Wei Chang
Journal:  Molecules       Date:  2022-02-27       Impact factor: 4.411
  10 in total

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