Literature DB >> 19461992

Total synthesis of atrochamins F, H, I, and J through cascade reactions.

K C Nicolaou1, Troy Lister, Ross M Denton, Christine F Gelin.   

Abstract

A concise and efficient cascade-based total synthesis of artochamins F, H, I, and J is described. The potential biogenetic connection between artochamin F, or a derivative thereof, and artochamins H, I, and J, through an unusual formal [2+2] cycloaddition process, was shown to be feasible. An alternative mechanism for this transformation is also proposed.

Entities:  

Year:  2008        PMID： 19461992      PMCID： PMC2597834          DOI： 10.1016/j.tet.2008.02.108

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


  68 in total

1.  Total synthesis of colombiasin A and determination of its absolute configuration.

Authors:  K C Nicolaou; G Vassilikogiannakis; W Mägerlein; R Kranich
Journal:  Chemistry       Date:  2001-12-17       Impact factor: 5.236

2.  Total synthesis of the CP-molecules (CP-263,114 and CP-225,917, phomoidrides B and A). 3. Completion and synthesis of advanced analogues.

Authors:  K C Nicolaou; Y-L Zhong; P S Baran; J Jung; H-S Choi; W H Yoon
Journal:  J Am Chem Soc       Date:  2002-03-13       Impact factor: 15.419

3.  The second total synthesis of diazonamide A.

Authors:  K C Nicolaou; Paraselli Bheema Rao; Junliang Hao; Mali Venkat Reddy; Gerasimos Rassias; Xianhai Huang; David Y-K Chen; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-17       Impact factor: 15.336

4.  Total synthesis of the proposed azaspiracid-1 structure, part 1: construction of the enantiomerically pure C1-C20, C21-C27, and C28-C40 fragments.

Authors:  K C Nicolaou; Yiwei Li; Noriaki Uesaka; Theocharis V Koftis; Stepan Vyskocil; Taotao Ling; Mugesh Govindasamy; Wenyuan Qian; Federico Bernal; David Y-K Chen
Journal:  Angew Chem Int Ed Engl       Date:  2003-08-11       Impact factor: 15.336

5.  Chemistry and biology of diazonamide A: first total synthesis and confirmation of the true structure.

Authors:  K C Nicolaou; David Y-K Chen; Xianhai Huang; Taotao Ling; Marco Bella; Scott A Snyder
Journal:  J Am Chem Soc       Date:  2004-10-13       Impact factor: 15.419

6.  Total synthesis and confirmation of the revised structures of azaspiracid-2 and azaspiracid-3.

Authors:  K C Nicolaou; Michael O Frederick; Goran Petrovic; Kevin P Cole; Eriketi Z Loizidou
Journal:  Angew Chem Int Ed Engl       Date:  2006-04-10       Impact factor: 15.336

7.  Total synthesis and structural elucidation of azaspiracid-1. Synthesis-based analysis of originally proposed structures and indication of their non-identity to the natural product.

Authors:  K C Nicolaou; David Y-K Chen; Yiwei Li; Noriaki Uesaka; Goran Petrovic; Theocharis V Koftis; Federico Bernal; Michael O Frederick; Mugesh Govindasamy; Taotao Ling; Petri M Pihko; Wenjun Tang; Stepan Vyskocil
Journal:  J Am Chem Soc       Date:  2006-02-22       Impact factor: 15.419

8.  Total synthesis of the CP-molecules (CP-263,114 and CP-225,917, phomoidrides B and A). 1. Racemic and asymmetric synthesis of bicyclo[4.3.1] key building blocks.

Authors:  K C Nicolaou; J Jung; W H Yoon; K C Fong; H-S Choi; Y He; Y-L Zhong; P S Baran
Journal:  J Am Chem Soc       Date:  2002-03-13       Impact factor: 15.419

9.  Artoindonesianin P, a new prenylated flavone with cytotoxic activity from Artocarpus lanceifolius.

Authors:  Euis Holisotan Hakim; Norio Aimi; Mariko Kitajima; Hiromitsu Takayama
Journal:  Fitoterapia       Date:  2002-12       Impact factor: 2.882

10.  New isoprenylated flavones, artochamins A--E, and cytotoxic principles from Artocarpus chama.

Authors:  Yong-Hong Wang; Ai-Jun Hou; Lei Chen; Dao-Feng Chen; Han-Dong Sun; Qin-Shi Zhao; Kenneth F Bastow; Yuka Nakanish; Xi-Hong Wang; Kuo-Hsiung Lee
Journal:  J Nat Prod       Date:  2004-05       Impact factor: 4.050
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  4 in total

1.  Rapid, stable, chemoselective labeling of thiols with Julia-Kocieński-like reagents: a serum-stable alternative to maleimide-based protein conjugation.

Authors:  Narihiro Toda; Shigehiro Asano; Carlos F Barbas
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-02       Impact factor: 15.336

2.  Stereoselective preparation of cyclobutanes with four different substituents: total synthesis and structural revision of pipercyclobutanamide A and piperchabamide G.

Authors:  Renhe Liu; Min Zhang; Thomas P Wyche; Gabrielle N Winston-McPherson; Tim S Bugni; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-19       Impact factor: 15.336

Review 3.  Recent advances in the synthesis of gem-dimethylcyclobutane natural products.

Authors:  Erin N Hancock; Johannes M Wiest; M Kevin Brown
Journal:  Nat Prod Rep       Date:  2019-10-16       Impact factor: 13.423

4.  Inspirations, discoveries, and future perspectives in total synthesis.

Authors:  K C Nicolaou
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354
  4 in total

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