(+)-Rimocidin synthetic studies. Construction of an advanced C(1-18) polyol fragment.
[structure: see text] The synthesis of an appropriately functionalized advanced C(1-18) polyol fragment of the mycosamine-glycosylated polyene macrolide, (+)-rimocidin (1), has been achieved in a highly efficient manner. Highlights of the strategy include the S(N)2/S(N)2' addition of dithiane anions to vinyl epoxides and the multicomponent linchpin union of 2-TBS-1,3-dithiane with two advanced epoxides.
Smith
Amos B
AB
Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Pitram
Suresh M
SM
Fuertes
Michael J
MJ
D000470:Alkaloids / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D011090:Polyenes / Q000138:chemical synthesis*; D011108:Polymers / Q000737:chemistry*; D011807:Quinolizines / Q000737:chemistry; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry
D000470:Alkaloids; D004852:Epoxy Compounds; D011090:Polyenes; D011108:Polymers; D011807:Quinolizines; D013457:Sulfur Compounds; C438055:dithiane; C024617:polyol; C003273:rimocidin