Literature DB >> 16706513

Formal total synthesis of the cytotoxic marine ascidian alkaloid haouamine A.

Jeannie H Jeong1, Steven M Weinreb.   

Abstract

[reaction: see text] Described is a convergent 13-step synthesis of a pentacyclic compound which has previously been transformed into haouamine A, therefore constituting a formal total synthesis of this unique marine alkaloid.

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Year:  2006        PMID： 16706513      PMCID： PMC2566532          DOI： 10.1021/ol060556c

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


  7 in total

1.  The first examples of ring-closing olefin metathesis of vinyl chlorides.

Authors:  Wenchun Chao; Steven M Weinreb
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

2.  Facile synthesis of the indeno-tetrahydropyridine core of haouamine A.

Authors:  Nicole D Smith; Joji Hayashida; Viresh H Rawal
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

3.  Synthesis of the 3-aza-[7]-paracyclophane core of haouamine A and B.

Authors:  Peter Wipf; Markus Furegati
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

4.  Total syntheses of (-)-haemanthidine, (+)-pretazettine, and (+)-tazettine.

Authors:  S W Baldwin; J S Debenham
Journal:  Org Lett       Date:  2000-01-27       Impact factor: 6.005

5.  Synthetic studies toward the haouamines.

Authors:  Marc A Grundl; Dirk Trauner
Journal:  Org Lett       Date:  2006-01-05       Impact factor: 6.005

6.  Haouamines A and B: a new class of alkaloids from the ascidian Aplidium haouarianum.

Authors:  Leda Garrido; Eva Zubía; María J Ortega; Javier Salvá
Journal:  J Org Chem       Date:  2003-01-24       Impact factor: 4.354

7.  Total synthesis of (+/-)-haouamine A.

Authors:  Phil S Baran; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2006-03-29       Impact factor: 15.419
  7 in total
  6 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.  Total synthesis of haouamine A: the indeno-tetrahydropyridine core.

Authors:  Noah Z Burns; Mikkel Jessing; Phil S Baran
Journal:  Tetrahedron       Date:  2009-08-15       Impact factor: 2.457

3.  Chemoselectivity: the mother of invention in total synthesis.

Authors:  Ryan A Shenvi; Daniel P O'Malley; Phil S Baran
Journal:  Acc Chem Res       Date:  2009-04-21       Impact factor: 22.384

4.  Scalable total synthesis and biological evaluation of haouamine A and its atropisomer.

Authors:  Noah Z Burns; Irina N Krylova; Rami N Hannoush; Phil S Baran
Journal:  J Am Chem Soc       Date:  2009-07-08       Impact factor: 15.419

5.  Mechanism of alkoxy groups substitution by Grignard reagents on aromatic rings and experimental verification of theoretical predictions of anomalous reactions.

Authors:  Gonzalo Jiménez-Osés; Anthony J Brockway; Jared T Shaw; K N Houk
Journal:  J Am Chem Soc       Date:  2013-04-22       Impact factor: 15.419

6.  Synthesis of a mitochondria-targeted spin trap using a novel Parham-type cyclization.

Authors:  Caroline Quin; Jan Trnka; Alison Hay; Michael P Murphy; Richard C Hartley
Journal:  Tetrahedron       Date:  2009-09-26       Impact factor: 2.457
  6 in total

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