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Synthesis of Tetrasubstituted β-Lactones

✍ Scribed by Cole Clissold; Clare L. Kelly; Kenneth W.M. Lawrie; Christine L. Willis

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
485 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

A versatile route for the synthesis of fi-lactones via oxidation of tetrasubstituted cyclopWanona is deseribed. Eachstepin thesyntbeticpatbway fromcis-2-oxabicyc3~3.3.O]ou-fi-en-2one to theketonesproceedswithexcellentregio-andstereoselectivity andin goodyield. Baeyer-Vi3tiger oxidationof tbe cyclopentanone21 witba furtbermetbylsubstituent at C-1'of tie side chin gives a single &lactone22 whereasa 3:1mixtureof regioisomers12 and 13 is obtainedfromtbe analogue11 with no substituentat C-1'. 0 1997ElsevierScienceLtd.

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For investigations concerning the selectivity of polyketide synthases (PKSs) which have been rationally engineered through genetic techniques the synthesis of substituted Slactones is of great importance. An enantiospecific route towards eight of the possible sixteen stereoisomers was developed whic