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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Synthesis of the carbocyclic skeleton of abyssomicins C and D.

[reaction: see text] 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 CHCl(3) 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.[1]


  1. Synthesis of the carbocyclic skeleton of abyssomicins C and D. Snider, B.B., Zou, Y. Org. Lett. (2005) [Pubmed]
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