Literature DB >> 11405719

Total synthesis of (-)-salicylihalamide A.

B B Snider1, F Song.   

Abstract

[see structure]. A 16-step synthesis of the novel cytotoxin salicylihalamide A (1E) has been achieved in 3.3% overall yield using ring closing metathesis to generate the macrolide and addition of (1Z,3Z)-hexadienylcuprate (2), which was generated in situ from ethylcuprate and acetylene, to alkenyl isocyanate 3 to form the side chain.

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Year:  2001        PMID: 11405719     DOI: 10.1021/ol015822v

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


  7 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

2.  Phosphate tether-mediated approach to the formal total synthesis of (-)-salicylihalamides A and B.

Authors:  Rambabu Chegondi; Mary M L Tan; Paul R Hanson
Journal:  J Org Chem       Date:  2011-04-19       Impact factor: 4.354

3.  Divalent and Multivalent Activation in Phosphate Triesters: A Versatile Method for the Synthesis of Advanced Polyol Synthons.

Authors:  Christopher D Thomas; James P McParland; Paul R Hanson
Journal:  European J Org Chem       Date:  2009-10-08

4.  Evaluating the potential of vacuolar ATPase inhibitors as anticancer agents and multigram synthesis of the potent salicylihalamide analog saliphenylhalamide.

Authors:  Sylvain Lebreton; Janis Jaunbergs; Michael G Roth; Deborah A Ferguson; Jef K De Brabander
Journal:  Bioorg Med Chem Lett       Date:  2008-07-05       Impact factor: 2.823

5.  A Biocatalytic Route to Highly Enantioenriched β-Hydroxydioxinones.

Authors:  Rick C Betori; Eric R Miller; Karl A Scheidt
Journal:  Adv Synth Catal       Date:  2017-03-02       Impact factor: 5.837

6.  A fluorous-tagged linker from which small molecules are released by ring-closing metathesis.

Authors:  Stuart G Leach; Christopher J Cordier; Daniel Morton; Gordon J McKiernan; Stuart Warriner; Adam Nelson
Journal:  J Org Chem       Date:  2008-03-08       Impact factor: 4.354

Review 7.  Marine-Derived Macrolides 1990-2020: An Overview of Chemical and Biological Diversity.

Authors:  Hairong Zhang; Jiabin Zou; Xiaoxue Yan; Junlong Chen; Xiujiao Cao; Jialing Wu; Yinghui Liu; Tingting Wang
Journal:  Mar Drugs       Date:  2021-03-25       Impact factor: 5.118

  7 in total

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