A formal synthesis of the auriside aglycon.
A highly convergent formal synthesis of the auriside aglycon was achieved. An indene-based thiazolidinethione chiral auxiliary was used for the construction of both the C1-C9 and C10-C17 fragments via acetate aldol reactions. A Meinwald reaction was utilized to install the stereocenter at C2, and a conjugated addition to an ynone was used to construct the C9-C11 enone.
Tello-Aburto
Rodolfo
R
Division of Medicine and Natural Products Chemistry, The University of Iowa, Iowa City, Iowa 52242, USA.
Olivo
Horacio F
HF
D000085:Acetates / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D053778:Thiazolidines / Q000737:chemistry
D000085:Acetates; D000447:Aldehydes; D018942:Macrolides; D053778:Thiazolidines; C515769:auriside A; C515770:auriside B; C033089:thiazoline-2-thione; C116609:3-hydroxybutanal