A new approach to macrocyclization via alkene formation in catalytic diazo decomposition. Synthesis of patulolides A and B.
[reaction: see text] Effective synthetic uses of bisdiazocarbonyl compounds for the selective construction of diverse macrocycles, including the synthesis of patulolides A and B, by catalytic "carbene dimer" formation are reported. Control of stereochemistry and efficient methods for product isomerization or kinetic isomer differentiation have been achieved.
Doyle
M P
MP
Department of Chemistry, University of Regina, Saskatchewan, Canada. mdoyle@u.arizona.edu
Hu
W
W
Phillips
I M
IM
Wee
A G
AG
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003979:Diazonium Compounds / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry
D000475:Alkenes; D000900:Anti-Bacterial Agents; D000893:Anti-Inflammatory Agents; D000935:Antifungal Agents; D003979:Diazonium Compounds; D007783:Lactones; C049726:patulolide B; C049725:patulolide A