Premium
Diastereoselective Synthesis of the A‐B‐C Tricyclic Ring Structure of Stemocurtisine
Author(s) -
Dau Xuan Duc,
Willis Anthony C.,
Pyne Stephen G.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501080
Subject(s) - chemistry , tricyclic , moiety , stereochemistry , ring (chemistry) , alkaloid , natural product , total synthesis , cleavage (geology) , ether , ether cleavage , iodide , vinyl ether , organic chemistry , polymer , geotechnical engineering , fracture (geology) , engineering , copolymer
The diastereoselective synthesis of the A‐B‐C tricyclic ring structure of the Stemona alkaloid stemocurtisine is described. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide. Attempts to prepare the C‐3a–C‐11 ether moiety of this alkaloid through a photochemically induced oxidative cyclization method were unsuccessful because of the cleavage of the A‐ring.