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Chemical Modification of a Highly Functionalized Taxane. The Consequences of an Absent Bridgehead Double Bond on Oxetane D-Ring Construction

An oxetane D-ring has been fused to the framework of the highly functionalized taxane 2. The synthetic route is based on a trimethylsilyl triflate-promoted epoxide-opening step, followed by stereocontrolled, regioreversed oxirane formation and reductive transposition of this intermediate with bis(cy...

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Published in:	Journal of organic chemistry 2003-03, Vol.68 (6), p.2282-2289
Main Authors:	Paquette, Leo A, Lo, Ho Yin
Format:	Article
Language:	English
Subjects:	Alicyclic compounds, terpenoids, prostaglandins, steroids Bridged-Ring Compounds - chemical synthesis Bridged-Ring Compounds - chemistry Catalysis Chemistry Combinatorial Chemistry Techniques Cyclization Exact sciences and technology Indicators and Reagents Molecular Structure Nuclear Magnetic Resonance, Biomolecular Organic chemistry Oxidation-Reduction Paclitaxel - chemistry Preparations and properties Structure-Activity Relationship Taxoids Terpenoids Thermodynamics
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description	An oxetane D-ring has been fused to the framework of the highly functionalized taxane 2. The synthetic route is based on a trimethylsilyl triflate-promoted epoxide-opening step, followed by stereocontrolled, regioreversed oxirane formation and reductive transposition of this intermediate with bis(cyclopentadienyl)titanium(III) chloride. This last key step provides for the convenient implementation of additional hydroxyl groups ultimately conducive to intramolecular SN2 reaction. Tangential features of the route outlined herein include specific rearrangement reactions and a retro-aldol cleavage of ring A.
doi_str_mv	10.1021/jo0206566
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source	American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects	Alicyclic compounds, terpenoids, prostaglandins, steroids Bridged-Ring Compounds - chemical synthesis Bridged-Ring Compounds - chemistry Catalysis Chemistry Combinatorial Chemistry Techniques Cyclization Exact sciences and technology Indicators and Reagents Molecular Structure Nuclear Magnetic Resonance, Biomolecular Organic chemistry Oxidation-Reduction Paclitaxel - chemistry Preparations and properties Structure-Activity Relationship Taxoids Terpenoids Thermodynamics
title	Chemical Modification of a Highly Functionalized Taxane. The Consequences of an Absent Bridgehead Double Bond on Oxetane D-Ring Construction
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