Literature DB >> 19461991

A Rh(II)-catalyzed cycloaddition approach towards the synthesis of komaroviquinone.

Albert Padwa1, Majid J Chughtai, Jutatip Boonsombat, Paitoon Rashatasakhon.   

Abstract

Using a rhodium(II)-catalyzed cyclization/cycloaddition sequence as the key reaction step, the icetexane core of komaroviquinone was constructed by an intramolecular dipolar-cycloaddition of a carbonyl ylide dipole across a tethered pi-bond. The ylide was arrived at by cyclization of a rhodium carbenoid intermediate onto a proximal ester group. Efforts towards the preparation of the required precursor for elaboration to the natural product are discussed.

Entities:  

Year:  2008        PMID： 19461991      PMCID： PMC2597821          DOI： 10.1016/j.tet.2008.01.129

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


  10 in total

1.  Cascade Processes of Metallo Carbenoids.

Authors:  Albert Padwa; M. David Weingarten
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  The asymmetric intramolecular Heck reaction in natural product total synthesis.

Authors:  Amy B Dounay; Larry E Overman
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

3.  Use of Conjugated Dienones in Cyclialkylations: The Total Syntheses of (+/-)-Barbatusol, (+/-)-Pisiferin, (+/-)-Deoxofaveline, (+/-)-Xochitlolone, and (+/-)-Faveline.

Authors:  George Majetich; Rodgers Hicks; Yong Zhang; Xinrong Tian; Terry Lee Feltman; Jing Fang; Sam Duncan
Journal:  J Org Chem       Date:  1996-11-15       Impact factor: 4.354

4.  Ga(III)-catalyzed cycloisomerization strategy for the synthesis of icetexane diterpenoids: total synthesis of (+/-)-salviasperanol.

Authors:  Eric M Simmons; Richmond Sarpong
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

5.  Stereoselective syntheses of (+/-)-komaroviquinone and (+/-)-faveline methyl ether through intramolecular Heck reaction.

Authors:  Sujaya Sengupta; Michael G B Drew; Ranjan Mukhopadhyay; Basudeb Achari; Asish Kr Banerjee
Journal:  J Org Chem       Date:  2005-09-16       Impact factor: 4.354

6.  Efficient construction of the oxatricyclo[6.3.1.0(0,0)]dodecane core of komaroviquinone using a cyclization/cycloaddition cascade of a rhodium carbenoid intermediate.

Authors:  Albert Padwa; Jutatip Boonsombat; Paitoon Rashatasakhon; Jerremey Willis
Journal:  Org Lett       Date:  2005-08-18       Impact factor: 6.005

7.  Epoxides and aziridines from diazoacetates via ylide intermediates.

Authors:  M P Doyle; W Hu; D J Timmons
Journal:  Org Lett       Date:  2001-03-22       Impact factor: 6.005

8.  Acid-catalyzed reactions of aromatic aldehydes with ethyl diazoacetate: an investigation on the synthesis of 3-hydroxy-2-arylacrylic acid ethyl esters.

Authors:  Matthew E Dudley; Md Monzur Morshed; Courtney L Brennan; M Shahidul Islam; M Syarhabil Ahmad; Mary-Rose Atuu; Bryan Branstetter; M Mahmun Hossain
Journal:  J Org Chem       Date:  2004-10-29       Impact factor: 4.354

9.  Divergence of carbonyl ylide reactions as a function of diazocarbonyl compound and aldehyde substituent: dioxolanes, dioxolenes, and epoxides.

Authors:  Albert E Russell; Jonathan Brekan; Luisa Gronenberg; Michael P Doyle
Journal:  J Org Chem       Date:  2004-08-06       Impact factor: 4.354

10.  New icetexane and 20 norabietane diterpenes with trypanocidal activity from Dracocephalum komarovi.

Authors:  Nahoko Uchiyama; Fumiyuki Kiuchi; Michiho Ito; Gisho Honda; Yoshio Takeda; Olimjon K Khodzhimatov; Ozodbek A Ashurmetov
Journal:  J Nat Prod       Date:  2003-01       Impact factor: 4.050
  10 in total
  2 in total

1.  Intramolecular carbenoid ylide forming reactions of 2-diazo-3-keto-4-phthalimidocarboxylic esters derived from methionine and cysteine.

Authors:  Marc Enßle; Stefan Buck; Roland Werz; Gerhard Maas
Journal:  Beilstein J Org Chem       Date:  2012-03-22       Impact factor: 2.883

2.  Synthesis, Structure-Activity Relationships, and Parasitological Profiling of Brussonol Derivatives as New Plasmodium falciparum Inhibitors.

Authors:  Camila S Barbosa; Anees Ahmad; Sarah El Chamy Maluf; Igor M R Moura; Guilherme E Souza; Giovanna A H Guerra; Roberto R Moraes Barros; Marcos L Gazarini; Anna C C Aguiar; Antonio C B Burtoloso; Rafael V C Guido
Journal:  Pharmaceuticals (Basel)       Date:  2022-06-30
  2 in total

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