Exploring symmetry-based logic for a synthesis of palau'amine.
A synthetic approach to palau'amine is described that exploits veiled symmetry in the structure. Bis-alkylidenes i have been prepared and found susceptible to halogenative desymmetrization using t-BuOCl. This oxidation forms the imbedded spirocyclopentane motif observed in the natural product. A host of atypical reactions and processes developed during these studies are discussed, as are plans for completing total syntheses of this compound class.
Li
Qingyi
Q
Department of Biochemistry, University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, USA.
Hurley
Paul
P
Ding
Hui
H
Roberts
Andrew G
AG
Akella
Radha
R
Harran
Patrick G
PG
D000470:Alkaloids / Q000737:chemistry; D003500:Cyclization; D019281:Dimerization; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry*; D015203:Reproducibility of Results; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000470:Alkaloids; D006146:Guanidines; D013141:Spiro Compounds; C438976:palau'amine