Synthesis of the C1-C13 fragment of leucascandrolide A.
[reaction: see text] The synthesis of the C1-C13 fragment 3 of leucascandrolide A has been completed utilizing a stereoselective and regioselective reductive cleavage of a highly functionalized spiroketal to incorporate the cis-2,6-disubstituted tetrahydropyan. The spiroketal was constructed by addition of a lithiated pyrone 5 to aldehyde 6.
Crimmins
M T
MT
Venable and Kenan Laboratories of Chemistry, The University of North Carolina at Chapel Hill, 27599-3290, USA. crimmins@email.unc.edu
Carroll
C A
CA
King
B W
BW
D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013816:Thermodynamics
D012717:Sesquiterpenes; C408748:leucascandrolide A