Literature DB >> 12929397

Concise synthesis of (+/-)-horsfiline and (+/-)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides.

Dimitrios E Lizos1, John A Murphy.   

Abstract

A brief, efficient and economical synthesis of the spiropyrrolidinyloxindoles, horsfiline and coerulescine, has been achieved, starting from itaconic acid and, respectively, p-anisidine or o-iodoaniline. Tandem radical cyclisation of iodoaryl alkenyl azides is the key step in both syntheses.

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Year:  2003        PMID： 12929397     DOI： 10.1039/b208114h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  8 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.  Preparation of 2,3-Disubstituted Indoles by Sequential Larock Heteroannulation and Silicon-Based Cross-Coupling Reactions.

Authors:  Scott E Denmark; John D Baird
Journal:  Tetrahedron       Date:  2009-04-18       Impact factor: 2.457

3.  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

Review 4.  Synthesis of indole derivatives as prevalent moieties present in selected alkaloids.

Authors:  Majid M Heravi; Zahra Amiri; Kosar Kafshdarzadeh; Vahideh Zadsirjan
Journal:  RSC Adv       Date:  2021-10-15       Impact factor: 4.036

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

6.  Stereospecific approach to the synthesis of ring-A oxygenated sarpagine indole alkaloids. Total synthesis of the dimeric indole alkaloid P-(+)-dispegatrine and six other monomeric indole alkaloids.

Authors:  Chitra R Edwankar; Rahul V Edwankar; Ojas A Namjoshi; Xuebin Liao; James M Cook
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354

Review 7.  Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review.

Authors:  Md Toufiqur Rahman; Veera V N Phani Babu Tiruveedhula; James M Cook
Journal:  Molecules       Date:  2016-11-14       Impact factor: 4.411

8.  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
  8 in total

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