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Functional Complementation Analysis (FCA): A Laboratory Exercise Designed and Implemented to Supplement the Teaching of Biochemical Pathways
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Short and versatile route to a key intermediate for lactacystin synthesis
Philip C Bulman Page1, A Sazali Hamzah, David C Leach
1Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, England. pcbpage@lboro.ac.uk
Abstract:
[reaction: see text] A key intermediate 14 for the synthesis of lactacystin 1 has been constructed in four steps and 33% overall yield. The key steps involve cyclization of a suitably functionalized glutamic acid derivative and concomitant alkylation of the resulting beta,beta-diketoester system, C-acylation of the cyclic alpha-amidoketone 9, and decarboxylbenzylation of 12. Alkylation of a related beta,beta-diketoester 5 was additionally achieved with several electrophiles.
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