Literature DB >> 17441074

A formal total synthesis of taxol aided by an automated synthesizer.

Takayuki Doi1, Shinichiro Fuse, Shigeru Miyamoto, Kazuoki Nakai, Daisuke Sasuga, Takashi Takahashi.   

Abstract

A 36-step synthesis was carried out in automated synthesizers to provide a synthetic key intermediate of taxol. A key step involved a microwave-assisted alkylation reaction to construct the ABC ring system from an AC precursor. Subsequent formation of the D ring afforded baccatin III, a well-known precursor of taxol.

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Year:  2006        PMID: 17441074     DOI: 10.1002/asia.200600156

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  19 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

Review 2.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

3.  Toward the Ideal Synthesis and Transformative Therapies: The Roles of Step Economy and Function Oriented Synthesis.

Authors:  Paul A Wender
Journal:  Tetrahedron       Date:  2013-06-07       Impact factor: 2.457

4.  Bioactive natural products: function first.

Authors:  Andrew J Phillips
Journal:  Nat Chem       Date:  2011-07-22       Impact factor: 24.427

5.  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

6.  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

Review 7.  The Molecular Industrial Revolution: Automated Synthesis of Small Molecules.

Authors:  Melanie Trobe; Martin D Burke
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-07       Impact factor: 15.336

8.  Total synthesis of taxane terpenes: cyclase phase.

Authors:  Yoshihiro Ishihara; Abraham Mendoza; Phil S Baran
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

9.  Automated synthesis of a library of triazolated 1,2,5-thiadiazepane 1,1-dioxides via a double aza-Michael strategy.

Authors:  Qin Zang; Salim Javed; David Hill; Farman Ullah; Danse Bi; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Conrad Santini; Michael G Organ; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2012-08-01       Impact factor: 3.784

10.  Scalable enantioselective total synthesis of taxanes.

Authors:  Abraham Mendoza; Yoshihiro Ishihara; Phil S Baran
Journal:  Nat Chem       Date:  2011-11-06       Impact factor: 24.427

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