(+)-Rimocidin synthetic studies: construction of the C(1-27) aglycone skeleton.
Assembly of the C(1-27) macrocyclic skeleton of rimocidinolide, the aglycone of (+)-rimocidin (1), has been achieved in convergent fashion. Key features of the synthetic strategy entail application of multicomponent Type I Anion Relay Chemistry (ARC), in conjunction with the S(N)2/S(N)2' reaction manifolds of vinyl epoxides, both employing 2-substituted 1,3-dithianes to construct the C(1-19) carbon backbone. Yamaguchi union of a C(20-27) vinyl borate ester, possessing the all-trans triene, with an advanced C(1-19) vinyl iodide followed by macrocyclization via Suzuki-Miyaura cross-coupling completed construction of the C(1-27) rimocidinolide skeleton.
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
Foley
Megan A
MA
Dong
Shuzhi
S
Orbin
Alia
A
D001881:Borates / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000737:chemistry*; D011090:Polyenes / Q000138:chemical synthesis / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry; D011807:Quinolizines / Q000737:chemistry; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry
D001881:Borates; D002264:Carboxylic Acids; D004852:Epoxy Compounds; D047028:Macrocyclic Compounds; D011090:Polyenes; D011714:Pyrans; D011807:Quinolizines; D013457:Sulfur Compounds; C438055:dithiane; C003273:rimocidin