Synthesis of (+)-patulolide C via an asymmetric hydroformylation/macrocyclization cascade.
A highly atom-economical total synthesis of (+)-patulolide C has been accomplished in three steps from the known (2R)-8-nonyn-2-ol in 49% overall yield and 93% de. A Rh(I)-catalyzed asymmetric hydroformylation (AHF)/ intramolecular Wittig olefination cascade was utilized to set the C4-hydroxyl stereochemistry and E-olefin geometry as well as form the macrolactone.
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1322, USA.
Roberto M
RM
Risi
Steven D
SD
Burke
D002384:Catalysis; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis; D018942:Macrolides; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
D006575:Heterocyclic Compounds, 3-Ring; D007783:Lactones; D018942:Macrolides; D014753:Vinyl Compounds; C049727:patulolide C; C011566:vinyl acetate