Assignment of absolute configuration to SCH 351448 via total synthesis.
The synthesis and absolute configuration of SCH 351448, an interesting ionophoric natural product, are reported herein. Mukaiyama aldol-Prins and segment-coupling Prins reactions were employed to construct the constituent tetrahydropyrans of SCH 351448. Efforts to assemble the C2-symmetric core of the natural product by a templated olefin metathesis strategy are described; however, a stepwise fragment assembly was ultimately utilized to complete the target molecule.
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Lael L
LL
Cheung
Shinji
S
Marumoto
Christopher D
CD
Anderson
Scott D
SD
Rychnovsky
D000475:Alkenes / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008847:Micromonospora / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D001688:Biological Products; D007783:Lactones; C451479:SCH 351448