Literature DB >> 20161191

Total synthesis of haouamine A: the indeno-tetrahydropyridine core.

Noah Z Burns1, Mikkel Jessing, Phil S Baran.   

Abstract

A full account of class="Gene">synthetic efforts towards the <class="Chemical">span class="Chemical">indeno-tetrahydropyridine core of haouamine A is presented. Initial failed strategies led to the unexpected discovery of a mild abnormal Chichibabin pyridine synthesis and provided knowledge and inspiration for the development of a cascade annulation that has enabled rapid and scalable access to the core in either racemic or enantiopure form.

Entities:  

Year:  2009        PMID: 20161191      PMCID: PMC2728496          DOI: 10.1016/j.tet.2009.05.075

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  17 in total

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

Authors:  Jeannie H Jeong; Steven M Weinreb
Journal:  Org Lett       Date:  2006-05-25       Impact factor: 6.005

2.  Palladium-catalyzed asymmetric allylic alkylation of alpha-aryl ketones.

Authors:  Barry M Trost; Gretchen M Schroeder; Jesper Kristensen
Journal:  Angew Chem Int Ed Engl       Date:  2002-09-16       Impact factor: 15.336

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.  On the origin of the haouamine alkaloids.

Authors:  Noah Z Burns; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Formal total synthesis of haouamine A.

Authors:  Tsuyoshi Taniguchi; Hisaaki Zaimoku; Hiroyuki Ishibashi
Journal:  J Org Chem       Date:  2009-03-20       Impact factor: 4.354

6.  Redox economy in organic synthesis.

Authors:  Noah Z Burns; Phil S Baran; Reinhard W Hoffmann
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

7.  Synthetic studies toward the haouamines.

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

8.  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

Review 9.  Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

Authors:  Huw M L Davies; James R Manning
Journal:  Nature       Date:  2008-01-24       Impact factor: 49.962

10.  Calculated chemical shifts as a fine tool of conformational analysis: an unambiguous solution for haouamine alkaloids.

Authors:  Anatoly M Belostotskii
Journal:  J Org Chem       Date:  2008-07-03       Impact factor: 4.354

View more
  1 in total

1.  One-Pot Phosphate-Mediated Synthesis of Novel 1,3,5-Trisubstituted Pyridinium Salts: A New Family of S. aureus Inhibitors.

Authors:  Thomas Pesnot; Markus C Gershater; Martin Edwards; John M Ward; Helen C Hailes
Journal:  Molecules       Date:  2017-04-12       Impact factor: 4.411

  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.