Studies towards a stereocontrolled synthesis of the tricarboxylate core of the zaragozic acids-squalestatins by a cycloaddition-rearrangement strategy

Reaction of diazoketodiester 11 with methyl glyoxylate in toluene in the presence of catalytic rhodium(II) acetate gives predominantly the 6,8- dioxabicyclo[3.2.1]octane 13. Acid-catalysed rearrangement of the corresponding alcohol 14 favours at equilibrium the 2,8- dioxabicyclo[3.2.1]octane skeleto...

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Main Authors: Hodgson, D, Villalonga-Barber, C
Format: Journal article
Language:English
Published: 2000
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author Hodgson, D
Villalonga-Barber, C
author_facet Hodgson, D
Villalonga-Barber, C
author_sort Hodgson, D
collection OXFORD
description Reaction of diazoketodiester 11 with methyl glyoxylate in toluene in the presence of catalytic rhodium(II) acetate gives predominantly the 6,8- dioxabicyclo[3.2.1]octane 13. Acid-catalysed rearrangement of the corresponding alcohol 14 favours at equilibrium the 2,8- dioxabicyclo[3.2.1]octane skeleton 15 of the zaragozic acids-squalestatins. (C) 2000 Elsevier Science Ltd.
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spelling oxford-uuid:3dc24b92-27ca-4144-9297-7f7ef645eb632022-03-26T14:21:18ZStudies towards a stereocontrolled synthesis of the tricarboxylate core of the zaragozic acids-squalestatins by a cycloaddition-rearrangement strategyJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:3dc24b92-27ca-4144-9297-7f7ef645eb63EnglishSymplectic Elements at Oxford2000Hodgson, DVillalonga-Barber, CReaction of diazoketodiester 11 with methyl glyoxylate in toluene in the presence of catalytic rhodium(II) acetate gives predominantly the 6,8- dioxabicyclo[3.2.1]octane 13. Acid-catalysed rearrangement of the corresponding alcohol 14 favours at equilibrium the 2,8- dioxabicyclo[3.2.1]octane skeleton 15 of the zaragozic acids-squalestatins. (C) 2000 Elsevier Science Ltd.
spellingShingle Hodgson, D
Villalonga-Barber, C
Studies towards a stereocontrolled synthesis of the tricarboxylate core of the zaragozic acids-squalestatins by a cycloaddition-rearrangement strategy
title Studies towards a stereocontrolled synthesis of the tricarboxylate core of the zaragozic acids-squalestatins by a cycloaddition-rearrangement strategy
title_full Studies towards a stereocontrolled synthesis of the tricarboxylate core of the zaragozic acids-squalestatins by a cycloaddition-rearrangement strategy
title_fullStr Studies towards a stereocontrolled synthesis of the tricarboxylate core of the zaragozic acids-squalestatins by a cycloaddition-rearrangement strategy
title_full_unstemmed Studies towards a stereocontrolled synthesis of the tricarboxylate core of the zaragozic acids-squalestatins by a cycloaddition-rearrangement strategy
title_short Studies towards a stereocontrolled synthesis of the tricarboxylate core of the zaragozic acids-squalestatins by a cycloaddition-rearrangement strategy
title_sort studies towards a stereocontrolled synthesis of the tricarboxylate core of the zaragozic acids squalestatins by a cycloaddition rearrangement strategy
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AT villalongabarberc studiestowardsastereocontrolledsynthesisofthetricarboxylatecoreofthezaragozicacidssqualestatinsbyacycloadditionrearrangementstrategy