Total synthesis of (-)-2-epi-peloruside A.
A convergent synthesis of (-)-2-epi-peloruside A has been achieved. Highlights include implementation of multicomponent type I anion relay chemistry (ARC) to unite 2-TBS-1,3-dithiane with two epoxides to construct the eastern hemisphere, a late-stage dithiane union to secure the complete, fully functionalized carbon backbone, and Yamaguchi macrolactonization, which led to (-)-2-epi-peloruside A via an unexpected epimerization at C(2).
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
Cox
Jason M
JM
Furuichi
Noriyuki
N
Kenesky
Craig S
CS
Zheng
Junying
J
Atasoylu
Onur
O
Wuest
William M
WM
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004852:Epoxy Compounds; D007783:Lactones; D011807:Quinolizines; D013457:Sulfur Compounds; C438055:dithiane; C414085:peloruside A