Journal
ORGANIC LETTERS
Volume 7, Issue 22, Pages 4939-4941Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0518941
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- NIGMS NIH HHS [GM50151] Funding Source: Medline
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[GRAPHICS] Intramolecular Diels-Alder substrate trienyl methylenebutenolide 5 was prepared in six steps by coupling 3-methoxy-4-methylenebutenolide (6) with trienone keto aldehyde 7. Heating 5 in CHCl3 for 2 d at 70 degrees C afforded 80% of a single Diels-Alder adduct 4 with the complete carbon skeleton of abyssomicin C. Addition of thiophenoxide to the enone double bond of 4 followed by an intramolecular Michael addition afforded 15 with the abyssomicin D carbon skeleton.
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