Literature DB >> 11735524

Azomethine ylide cycloaddition/reductive heterocyclization approach to oxindole alkaloids: asymmetric synthesis of (-)-horsfiline.

G Cravotto1, G B Giovenzana, T Pilati, M Sisti, G Palmisano.   

Abstract

The intermolecular [3 + 2] annulation of azomethine ylides with 2(2-nitrophenyl)acrylate dienophiles followed by reductive heterocyclization affords the spiro(indole-pyrrolidine) ring system. Hence, this enable us to accomplish a concise and highly enantioselective synthesis of (-)-horsfiline 1, based on chiral auxiliary-directed pi-face discrimination in the 1,3-dipolar cycloaddition of (1S,2R)-2-phenyl-1-cyclohexyl ester 4f with N-methylazomethine ylide.

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Year:  2001        PMID： 11735524     DOI： 10.1021/jo015854w

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


  12 in total

1.  Rh(II)2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides.

Authors:  Ashley L Pumphrey; Huijun Dong; Tom G Driver
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

2.  Palladium asymmetric allylic alkylation of prochiral nucleophiles: horsfiline.

Authors:  Barry M Trost; Megan K Brennan
Journal:  Org Lett       Date:  2006-05-11       Impact factor: 6.005

3.  Synthesis of a γ-lactam library via formal cycloaddition of imines and substituted succinic anhydrides.

Authors:  Darlene Q Tan; Amy L Atherton; Austin J Smith; Cristian Soldi; Katherine A Hurley; James C Fettinger; Jared T Shaw
Journal:  ACS Comb Sci       Date:  2012-02-10       Impact factor: 3.784

4.  Ethyl 3'-(2,4-dichloro-phen-yl)-5'-hydr-oxy-5'-methyl-4',5'-dihydro-spiro-[fluorene-9,2'(3'H)-furan]-4'-carboxyl-ate.

Authors:  M Nizammohideen; S Thenmozhi; A Subbiahpandi; G Savitha; P T Perumal
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-04-08

5.  Total synthesis of (±)-coerulescine and (±)-horsfiline.

Authors:  Mukund G Kulkarni; Attrimuni P Dhondge; Sanjay W Chavhan; Ajit S Borhade; Yunnus B Shaikh; Deekshaputra R Birhade; Mayur P Desai; Nagorao R Dhatrak
Journal:  Beilstein J Org Chem       Date:  2010-09-27       Impact factor: 2.883

Review 6.  Molecular diversity of spirooxindoles. Synthesis and biological activity.

Authors:  Tetyana L Pavlovska; Ruslan Gr Redkin; Victoria V Lipson; Dmytro V Atamanuk
Journal:  Mol Divers       Date:  2015-09-29       Impact factor: 2.943

7.  (1S,1'S,2'R,4a'S,9a'S,9b'R)-1'-Acet-yloxy-2,4'-dioxo-2',4',4a',7',8',9',9a',9b'-octa-hydro-1'H,2H-spiro-[ace-naphthyl-ene-1,5'-pyrano[4,3-a]pyrrolizin]-2'-ylmethyl acetate.

Authors:  S Santhiya; J Naga Siva Rao; R Raghunathan; N Latha; S Lakshmi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-10-02

8.  3''-(2-Fluoro-benzyl-idene)-4'-(2-fluoro-phen-yl)-1'-methyl-dispiro-[acenaphthyl-ene-1,2'-pyrrolidine-3',1''-cyclo-penta-ne]-2,2''-dione.

Authors:  Gao-Zhi Chen; Xiao-Yan Wei; Yi Wang; Lu-Qing Ren; Xiao-Kun Li
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-01-19

9.  Crystal structure of 5''-(4-chloro-benzyl-idene)-4'-(4-chloro-phen-yl)-1'-methyltri-spiro[acenapthylene-1,2'-pyrrolidine-3',1''-cyclo-hexane-3'',2'''-[1,3]dioxane]-2(1H),6''-dione.

Authors:  Kuppan Chandralekha; Deivasigamani Gavaskar; Adukamparai Rajukrishnan Sureshbabu; Srinivasakannan Lakshmi
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-10-03

10.  A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide.

Authors:  Mitsuhiro Ueda; Yoshitaka Uenoyama; Nozomi Terasoma; Shoko Doi; Shoji Kobayashi; Ilhyong Ryu; John A Murphy
Journal:  Beilstein J Org Chem       Date:  2013-07-05       Impact factor: 2.883
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