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.
Snider
Barry B
BB
Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA. snider@brandeis.edu
Zou
Yefen
Y
D000146:Acids, Carbocyclic / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D000146:Acids, Carbocyclic; D019086:Bridged Bicyclo Compounds, Heterocyclic; C509797:abyssomicin C; C512805:abyssomicin D