Enantioselective total synthesis of (-)-clavosolide B.
Enantioselective synthesis of 2, a revised structure for (-)-clavosolide B, was accomplished by a convergent approach, where syn-selective aldol, hydroxy-directed cyclopropanation, Mitsunobu inversion, Schmidt-type glycosylation, and macrolactonization reactions were utilized as key reactions. Comparison of 1H and 13C NMR spectra and optical rotation measurement confirmed the relative and absolute stereochemistry of clavosolide B (2).
Son
Jung Beom
JB
Department of Chemistry, Sogang University, Shinsoo-dong 1, Mapo-gu, Seoul 121-742, Korea.
Hwang
Min-ho
MH
Lee
Wonsun
W
Lee
Duck-Hyung
DH
D000818:Animals; D007096:Imidoesters / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism