Enantioselective synthesis of the C18-C25 segment of lasonolide A by an oxonia-cope prins cascade.
[reaction: see text] A 2-oxonia-Cope Prins cascade was developed that led to a facile and stereoselective synthesis of the C18-C25 segment of lasonolide A. The strategy nicely handles the introduction of the quaternary center in the tetrahydropyran ring, and all of the stereogenic centers in the product arise from a single stereocenter introduced in a catalytic enantioselective reaction.
Dalgard
Jackline E
JE
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA.
Rychnovsky
Scott D
SD
D000818:Animals; D002384:Catalysis; D003500:Cyclization; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D018942:Macrolides; D011714:Pyrans; C450700:lasonolide A