Literature DB >> 12000281

Synthesis of alkaloid 223A and a structural revision.

Naoki Toyooka1, Ayako Fukutome, Hideo Nemoto, John W Daly, Thomas F Spande, H Martin Garraffo, Tetsuo Kaneko.   

Abstract

[structure: see text] Synthesis of alkaloid 223A has been achieved by sequential use of our original conjugate addition reaction to enaminoesters as the key step. The proposed structure for natural 223A (A, absolute configuration unknown) was revised to B, and the relative stereostructure was determined to be 5R*,6R*,8R*,9S* by the present synthesis.

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Year:  2002        PMID： 12000281     DOI： 10.1021/ol025775m

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


  7 in total

1.  Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

Authors:  Carolyn A Leverett; Michael P Cassidy; Albert Padwa
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

2.  Bioactive alkaloids of frog skin: combinatorial bioprospecting reveals that pumiliotoxins have an arthropod source.

Authors:  John W Daly; Tetsuo Kaneko; Jason Wilham; H Martin Garraffo; Thomas F Spande; Alex Espinosa; Maureen A Donnelly
Journal:  Proc Natl Acad Sci U S A       Date:  2002-10-14       Impact factor: 11.205

3.  Scheloribatid mites as the source of pumiliotoxins in dendrobatid frogs.

Authors:  Wataru Takada; Tomoyo Sakata; Satoshi Shimano; Yoshinari Enami; Naoki Mori; Ritsuo Nishida; Yasumasa Kuwahara
Journal:  J Chem Ecol       Date:  2005-09-28       Impact factor: 2.626

4.  Enantioselective rhodium-catalyzed [2 + 2 + 2] cycloadditions of terminal alkynes and alkenyl isocyanates: mechanistic insights lead to a unified model that rationalizes product selectivity.

Authors:  Derek M Dalton; Kevin M Oberg; Robert T Yu; Ernest E Lee; Stéphane Perreault; Mark Emil Oinen; Melissa L Pease; Guillaume Malik; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

5.  Asymmetric total synthesis of alkaloids 223A and 6-epi-223A.

Authors:  Partha Ghosh; Weston R Judd; Timothy Ribelin; Jeffrey Aubé
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005

6.  Intermolecular [3+3] ring expansion of aziridines to dehydropiperi-dines through the intermediacy of aziridinium ylides.

Authors:  Josephine Eshon; Kate A Nicastri; Steven C Schmid; William T Raskopf; Ilia A Guzei; Israel Fernández; Jennifer M Schomaker
Journal:  Nat Commun       Date:  2020-03-09       Impact factor: 14.919

7.  Total Synthesis of Decahydroquinoline Poison Frog Alkaloids ent-cis-195A and cis-211A.

Authors:  Takuya Okada; Naizhen Wu; Katsuki Takashima; Jungoh Ishimura; Hiroyuki Morita; Takuya Ito; Takeshi Kodama; Yuhei Yamasaki; Shin-Ichi Akanuma; Yoshiyuki Kubo; Ken-Ichi Hosoya; Hiroshi Tsuneki; Tsutomu Wada; Toshiyasu Sasaoka; Takahiro Shimizu; Hideki Sakai; Linda P Dwoskin; Syed R Hussaini; Ralph A Saporito; Naoki Toyooka
Journal:  Molecules       Date:  2021-12-12       Impact factor: 4.411
  7 in total

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