Stereoselective syntheses of rolliniastatin 1, rollimembrin, and membranacin.
A radical cyclization of beta-alkoxyvinyl sulfoxides-Pummerer rearrangement-allylation protocol was successfully applied to the synthesis of the threo/cis/threo/cis/erythro bis-oxolane moiety in rolliniastatin 1 (1), rollimembrin (2), and membranacin (3).
Keum
Gyochang
G
Department of Chemistry, College of Natural Sciences, Seoul National University NS60, Seoul 151-747, Korea.
Hwang
Cheol Hee
CH
Kang
Soon Bang
SB
Kim
Youseung
Y
Lee
Eun
E
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D010944:Plants / Q000737:chemistry; D012639:Seeds / Q000737:chemistry; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; D013454:Sulfoxides; D014753:Vinyl Compounds; C504101:membranacin; C504102:rollimembrin; C061022:bullatacin