Formal synthesis of palmerolide A, featuring alkynogenic fragmentation and syn-selective vinylogous aldol chemistry.
An enantioselective route to palmerolide A is described. The approach features original syntheses of three subunits, which are then assembled to produce a known late-stage intermediate and formally provide the highest overall yield of the natural product reported to date. Recent innovations in alkynogenic fragmentation and vinylogous aldol methodology figure prominently in the synthesis of the C1-C15 and C16-C25 subunits, respectively.
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, United States.
Marilda P
MP
Lisboa
David M
DM
Jones
Gregory B
GB
Dudley
D000447:Aldehydes / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D001688:Biological Products; D018942:Macrolides; C522534:palmerolide A; C116609:3-hydroxybutanal