Literature DB >> 19637860

Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B.

Naoki Toyooka1, Dejun Zhou, Hideo Nemoto, Yasuhiro Tezuka, Shigetoshi Kadota, Nirina R Andriamaharavo, H Martin Garraffo, Thomas F Spande, John W Daly.   

Abstract

An efficient and flexible synthesis of poison-frog alkaloids 251O and trans-223B has been achieved by using for both alkaloids an enantiodivergent process starting from the common lactam 1. The relative stereochemistry of 251O and trans-223B was determined to be 7 (R = n-C(7)H(15), R' = n-Pr) and 14 by the present enantioselective synthesis.

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Year:  2009        PMID： 19637860      PMCID： PMC2747258          DOI： 10.1021/jo901100m

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  14 in total

1.  Total synthesis of pyrrolizidines 223H', 239K', 265H', and 267H' found in Madagascan frogs (Mantella) and their affinities for nicotinic acetylcholine receptor.

Authors:  H Takahata; S Takahashi; N Azer; A T Eldefrawi; M E Eldefrawi
Journal:  Bioorg Med Chem Lett       Date:  2000-06-05       Impact factor: 2.823

2.  Batrachotoxin alkaloids from passerine birds: a second toxic bird genus (Ifrita kowaldi) from New Guinea.

Authors:  J P Dumbacher; T F Spande; J W Daly
Journal:  Proc Natl Acad Sci U S A       Date:  2000-11-21       Impact factor: 11.205

3.  Ernest Guenther award in chemistry of natural products. Amphibian skin: a remarkable source of biologically active arthropod alkaloids.

Authors:  John W Daly
Journal:  J Med Chem       Date:  2003-02-13       Impact factor: 7.446

4.  Homobatrachotoxin in the genus Pitohui: chemical defense in birds?

Authors:  J P Dumbacher; B M Beehler; T F Spande; H M Garraffo; J W Daly
Journal:  Science       Date:  1992-10-30       Impact factor: 47.728

Review 5.  Alkaloids from amphibian skin: a tabulation of over eight-hundred compounds.

Authors:  John W Daly; Thomas F Spande; H Martin Garraffo
Journal:  J Nat Prod       Date:  2005-10       Impact factor: 4.050

6.  Total synthesis of pinnamine and anatoxin-a via a common intermediate. A caveat on the anatoxin-a endgame.

Authors:  Thomas Hjelmgaard; Inger Søtofte; David Tanner
Journal:  J Org Chem       Date:  2005-07-08       Impact factor: 4.354

7.  Alkaloids from bufonid toads (Melanophryniscus): decahydroquinolines, pumiliotoxins and homopumiliotoxins, indolizidines, pyrrolizidines, and quinolizidines.

Authors:  H M Garraffo; T F Spande; J W Daly; A Baldessari; E G Gros
Journal:  J Nat Prod       Date:  1993-03       Impact factor: 4.050

8.  Alkaloids indolizidine 235B', quinolizidine 1-epi-207I, and the tricyclic 205B are potent and selective noncompetitive inhibitors of nicotinic acetylcholine receptors.

Authors:  Hiroshi Tsuneki; Yueren You; Naoki Toyooka; Syota Kagawa; Soushi Kobayashi; Toshiyasu Sasaoka; Hideo Nemoto; Ikuko Kimura; John A Dani
Journal:  Mol Pharmacol       Date:  2004-07-16       Impact factor: 4.436

9.  Synthesis of poison-frog alkaloids 233A, 235U, and 251AA and their inhibitory effects on neuronal nicotinic acetylcholine receptors.

Authors:  Naoki Toyooka; Soushi Kobayashi; Dejun Zhou; Hiroshi Tsuneki; Tsutomu Wada; Hideki Sakai; Hideo Nemoto; Toshiyasu Sasaoka; H Martin Garraffo; Thomas F Spande; John W Daly
Journal:  Bioorg Med Chem Lett       Date:  2007-08-26       Impact factor: 2.823

10.  Enantioselective syntheses of (-)- and (+)-monomorine I.

Authors:  Naoki Toyooka; Dejun Zhou; Hideo Nemoto
Journal:  J Org Chem       Date:  2008-05-29       Impact factor: 4.354
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  1 in total

1.  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
  1 in total

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