Synthesis of the taxol core via catalytic asymmetric 1,4-addition of an Alkylzirconium Nucleophile

Synthesis of the taxol core via catalytic asymmetric 1,4-addition of an Alkylzirconium Nucleophile

The Taxol core was prepared in five steps via a key copper-catalyzed asymmetric conjugate addition trapping sequence. The use of a bromodiene-derived alkylzirconium nucleophile followed by trapping with POCl3/DMF gave a highly functionalized intermediate featuring a quaternary center in 69% yield wi...

पूर्ण विवरण

ग्रंथसूची विवरण
मुख्य लेखकों:	Wang, JYJ, Fletcher, S
स्वरूप:	Journal article
भाषा:	English
प्रकाशित:	American Chemical Society 2020

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प्रकाशित: (2014)

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Formation of quaternary centers by copper-catalyzed asymmetric conjugate addition of alkylzirconium reagents.
द्वारा: Sidera, M, और अन्य
प्रकाशित: (2013)

Acyclic quaternary centers from asymmetric conjugate addition of alkylzirconium reagents to linear trisubstituted enones
द्वारा: Gao, Z, और अन्य
प्रकाशित: (2016)

Copper-catalyzed asymmetric conjugate addition of alkylzirconium reagents to cyclic enones to form quaternary centers.
द्वारा: Roth, P, और अन्य
प्रकाशित: (2014)

Asymmetric conjugate addition of alkylzirconium reagents to α,β-unsaturated thioesters: access to fragrances and acyclic stereochemical arrays
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Asymmetric nucleophilic addition to vinylphosphonamidates (Part IV)
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द्वारा: Bunnage, M, और अन्य
प्रकाशित: (1994)

Cu-catalyzed asymmetric addition of sp²-hybridized zirconium nucleophiles to racemic allyl bromides.
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द्वारा: Lu, G., और अन्य
प्रकाशित: (2018)

Non-stabilized nucleophiles in cu-catalyzed asymmetric synthesis
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प्रकाशित: (2016)

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द्वारा: Gribble, Michael William, और अन्य
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Streamlined synthesis of taxol analogues
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प्रकाशित: (2017)

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द्वारा: Zhongwen Sun, और अन्य
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द्वारा: Chengshuai Yang, और अन्य
प्रकाशित: (2024-03-01)

Asymmetric electrophilic fluorocyclization with carbon nucleophiles.
द्वारा: Wolstenhulme, JR, और अन्य
प्रकाशित: (2013)

Asymmetric Synthesis of alpha-Substituted Benzyl Alcohols via the Stereoselective Addition of Nucleophiles to Homochiral Tricarbonyl(eta(6)-o-triisopropylsilylbenzaldehyde)chromium(0)
द्वारा: Davies, S, और अन्य
प्रकाशित: (1989)

β-Chloroaldehydes from trapping zirconium enolates produced in asymmetric 1,4-additions
द्वारा: Wang, J, और अन्य
प्रकाशित: (2018)

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Non-stabilized nucleophiles in Cu-catalysed dynamic kinetic asymmetric allylic alkylation
द्वारा: You, H, और अन्य
प्रकाशित: (2015)

Catalytic asymmetric synthesis /
द्वारा: Ojima, Iwao, 1945-
प्रकाशित: (2000)

Catalytic asymmetric synthesis /
द्वारा: Ojima, Iwao, 1945-
प्रकाशित: (c201)

Catalytic asymmetric synthesis /
द्वारा: Ojima Iwao
प्रकाशित: (1993)

An investigation of nucleophilic substitution reactions of 2,3-dichloro-1,4-naphthoquinone with various nucleophilic reagents
द्वारा: Ibis Cemil, और अन्य
प्रकाशित: (2015-01-01)

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द्वारा: Davies, S, और अन्य
प्रकाशित: (1990)

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द्वारा: Davies, S, और अन्य
प्रकाशित: (2009)

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द्वारा: Gao, Z, और अन्य
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