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- Title
Total Synthesis of Mycophenolic Acid by a Palladium-Catalyzed Decarboxylative Allylation and Biomimetic Aromatization Sequence.
- Authors
Brookes, Paul A.; Cordes, Jens; White, Andrew J. P.; Barrett, Anthony G. M.
- Abstract
This paper describes the total synthesis of the fungal natural product mycophenolic acid through palladium-catalyzed allylation, biomimetic cyclization, and aromatization. Methyl (4 E)-6-hydroxy-4-methylhex-4-enoate, which was converted in four steps into the key diketo ester dioxinone via two selective C-acylation reactions, was transformed into a resorcylate. Subsequent phenol methylation, lactonization, iodo-ether formation, and halogenation gave a tricyclic intermediate. Palladium-catalyzed cross-coupling with DABCO-(AlMe3)2 and saponification gave mycophenolic acid. An alternative approach with early stage arene methyl incorporation unexpectedly resulted in the formation of a γ-pyrone.
- Subjects
MYCOPHENOLIC acid; CHEMICAL synthesis; PALLADIUM catalysts; ALLYLATION; RING formation (Chemistry); AROMATIZATION; ACYLATION; SAPONIFICATION
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 32, p7313
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201300974