Literature DB >> 12688739

Synthesis of the apratoxin 2,4-disubstituted thiazoline via an intramolecular aza-Wittig reaction.

Jiehao Chen1, Craig J Forsyth.   

Abstract

[reaction: see text] In developing a synthetic entry to the thiazoline-containing domain of the apratoxin natural products, we converted vicinal azido-thiolesters into 2,4-disubstituted thiazolines via sequential one-pot Staudinger reduction/aza-Wittig reaction. This method of de novo thiazoline formation provides a mild and versatile process that is particularly well suited to acid-sensitive substrates.

Entities:  

Year:  2003        PMID： 12688739     DOI： 10.1021/ol0342148

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


  10 in total

1.  The azido acid approach to beta-peptides: parallel synthesis of a tri-beta-peptide library by fluorous tagging.

Authors:  Xiao Wang; Scott G Nelson; Dennis P Curran
Journal:  Tetrahedron       Date:  2007-07-02       Impact factor: 2.457

2.  Synthesis of 1,2,4-triazines and the triazinoisoquinolinedione DEF ring system of noelaquinone.

Authors:  Liming Cao; John P Maciejewski; Stephan Elzner; David Amantini; Peter Wipf
Journal:  Org Biomol Chem       Date:  2012-04-04       Impact factor: 3.876

3.  Evolved diversification of a modular natural product pathway: apratoxins F and G, two cytotoxic cyclic depsipeptides from a Palmyra collection of Lyngbya bouillonii.

Authors:  Kevin Tidgewell; Niclas Engene; Tara Byrum; Joseph Media; Takayuki Doi; Fred A Valeriote; William H Gerwick
Journal:  Chembiochem       Date:  2010-07-05       Impact factor: 3.164

4.  Total syntheses of the histone deacetylase inhibitors largazole and 2-epi-largazole: application of N-heterocyclic carbene mediated acylations in complex molecule synthesis.

Authors:  Bo Wang; Po-Hsien Huang; Ching-Shih Chen; Craig J Forsyth
Journal:  J Org Chem       Date:  2011-01-18       Impact factor: 4.354

5.  Total synthesis of the marine cyanobacterial cyclodepsipeptide apratoxin A.

Authors:  Jiehao Chen; Craig J Forsyth
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-01       Impact factor: 11.205

6.  Synthesis of aza-analogues of the glycosylated tyrosine portion of mannopeptimycin-E.

Authors:  Sanjeeva R Guppi; George A O'Doherty
Journal:  J Org Chem       Date:  2007-05-26       Impact factor: 4.354

7.  One-Carbon Insertion and Polarity Inversion Enabled a Pyrrole Strategy to the Total Syntheses of Pyridine-Containing Lycopodium Alkaloids: Complanadine A and Lycodine.

Authors:  Donghui Ma; Brandon S Martin; Katelyn S Gallagher; Takeru Saito; Mingji Dai
Journal:  J Am Chem Soc       Date:  2021-09-27       Impact factor: 16.383

8.  Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam.

Authors:  Yang Yang; Yu Bai; Siyuan Sun; Mingji Dai
Journal:  Org Lett       Date:  2014-11-20       Impact factor: 6.005

9.  FrpA is the outer membrane piscibactin transporter in Vibrio anguillarum: structural elements in synthetic piscibactin analogues required for transport.

Authors:  Marta A Lages; M Carmen de la Fuente; Lucía Ageitos; Diana Martínez-Matamoros; Jaime Rodríguez; Miguel Balado; Carlos Jiménez; Manuel L Lemos
Journal:  J Biol Inorg Chem       Date:  2021-11-18       Impact factor: 3.358

Review 10.  Case studies of the synthesis of bioactive cyclodepsipeptide natural products.

Authors:  Sara C Stolze; Markus Kaiser
Journal:  Molecules       Date:  2013-01-24       Impact factor: 4.411
  10 in total

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