Literature DB >> 26010812

Synthesis of Paclitaxel. 1. Synthesis of the ABC Ring of Paclitaxel by SmI2-Mediated Cyclization.

Keisuke Fukaya1, Yuta Tanaka1, Ayako C Sato1, Keisuke Kodama1, Hirohisa Yamazaki1, Takeru Ishimoto1, Yasuyoshi Nozaki1, Yuki M Iwaki1, Yohei Yuki1, Kentaro Umei1, Tomoya Sugai1, Yu Yamaguchi1, Ami Watanabe1, Takeshi Oishi2, Takaaki Sato1, Noritaka Chida1.   

Abstract

A convergent synthesis of the ABC ring of antitumor natural product paclitaxel (Taxol) is described. SmI2-mediated reductive cyclization of an allylic benzoate possessing an aldehyde function, synthesized from tri-O-acetyl-d-glucal and 1,3-cyclohexanedione, smoothly afforded the highly strained 6-8-6 tricarbocyclic structure in 66% yield.

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Year:  2015        PMID： 26010812     DOI： 10.1021/acs.orglett.5b01173

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


  8 in total

1.  Chemistry: Why synthesize?

Authors:  Philip Ball
Journal:  Nature       Date:  2015-12-17       Impact factor: 49.962

2.  Short, Enantioselective Total Synthesis of Highly Oxidized Taxanes.

Authors:  Changxia Yuan; Yehua Jin; Nathan C Wilde; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-30       Impact factor: 15.336

3.  Practical synthesis of the C-ring precursor of paclitaxel from 3-methoxytoluene.

Authors:  Keisuke Fukaya; Yu Yamaguchi; Ami Watanabe; Hiroaki Yamamoto; Tomoya Sugai; Takeshi Sugai; Takaaki Sato; Noritaka Chida
Journal:  J Antibiot (Tokyo)       Date:  2016-02-10       Impact factor: 2.649

4.  Crystal structure of (+)-(1S,5S,6S,7S,10S,11S,16S)-16-hy-droxy-7-(meth-oxy-meth-oxy)-11,15,18,18-tetra-methyl-3,13-dioxo-2,4-dioxa-tetra-cyclo[12.3.1.01,5.06,11]octa-dec-14-en-10-yl benzoate.

Authors:  Takeshi Oishi; Keisuke Fukaya; Takaaki Sato; Noritaka Chida
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2021-11-04

5.  Crystal structure of (±)-(7RS,8SR)-7-methyl-1,4-dioxa-spiro-[4.5]decane-7,8-diol.

Authors:  Takeshi Oishi; Hiroaki Yamamoto; Tomoya Sugai; Keisuke Fukaya; Yu Yamaguchi; Ami Watanabe; Takaaki Sato; Noritaka Chida
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-09-17

6.  Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives.

Authors:  Cong Ma; Aurélien Letort; Rémi Aouzal; Antonia Wilkes; Gourhari Maiti; Louis J Farrugia; Louis Ricard; Joëlle Prunet
Journal:  Chemistry       Date:  2016-04-08       Impact factor: 5.236

Review 7.  Transgenesis as a Tool for the Efficient Production of Selected Secondary Metabolites from in Vitro Plant Cultures.

Authors:  Tomasz Kowalczyk; Joanna Wieczfinska; Ewa Skała; Tomasz Śliwiński; Przemysław Sitarek
Journal:  Plants (Basel)       Date:  2020-01-21

Review 8.  Current Perspectives on Taxanes: Focus on Their Bioactivity, Delivery and Combination Therapy.

Authors:  Jan Škubník; Vladimíra Pavlíčková; Tomáš Ruml; Silvie Rimpelová
Journal:  Plants (Basel)       Date:  2021-03-17
  8 in total

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