Application of the intramolecular vinylogous Morita-Baylis-Hillman reaction toward the synthesis of the spinosyn A tricyclic nucleus.
[reaction: see text] A concise synthesis of the spinosyn A tricyclic nucleus 27 has been developed by a route featuring a one-pot tandem intramolecular Diels-Alder reaction and intramolecular vinylogous Morita-Baylis-Hillman cyclization in which five stereocenters in tricycle 10 are set with excellent selectivity.
Mergott
Dustin J
DJ
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055.
Frank
Scott A
SA
Roush
William R
WR
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D003500:Cyclization; D007306:Insecticides / Q000138:chemical synthesis; D018942:Macrolides; D016930:Saccharopolyspora / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
D000900:Anti-Bacterial Agents; D007306:Insecticides; D018942:Macrolides; D014753:Vinyl Compounds; C114883:spinosyn A