Enantioselective total synthesis of (+)-leucascandrolide A macrolactone.
[reaction: see text] The enantioselective synthesis of the (+)-leucascandrolide A macrolactone has been achieved in 20 linear steps from 1,3-propanediol. The key steps in the synthesis are a reductive cleavage of bicyclic ketal 5 to establish the C15 stereogenic center and a diastereoselective aldol of the boron enolate of methyl ketone 3 to aldehyde 4 in preparation for a heteroconjugate addition for the introduction of the C3 stereocenter.
Crimmins
Michael T
MT
Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, 27599, USA. crimmins@email.unc.edu
Siliphaivanh
Phieng
P
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D007659:Ketones; D012717:Sesquiterpenes; C408748:leucascandrolide A