Journal
ORGANIC LETTERS
Volume 13, Issue 14, Pages 3636-3639Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol201283n
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Funding
- Eli Lilly
- Amgen
- National Institutes of Health, National Institute of General Medical Sciences [R01 GM077379]
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A new protecting-group-free synthesis of the marine monocyclic ether (+)-brevisamide is reported. The enantioselective synthesis utilizes a key asymmetric Henry reaction and an Achmatowicz rearrangement for the formation of the tetrahydropyran ring. A penultimate Stille cross-coupling allows for an efficient installation of the conjugated (E,E)-diene side chain ultimately delivering (+)-brevisamide.
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