op1c00295_si_001.pdf (2.85 MB)
Synthesis of the C1–C13 Fragment of Eribulin on a Kilogram Scale
journal contribution
posted on 2021-12-14, 13:04 authored by Seong
Taek Kim, Yongseo Park, Namhyeon Kim, Jaeun Gu, Wongyoung Son, Jisu Hur, KangHee Lee, Areum Baek, Ju Young Song, U Bin Kim, Kee-Young Lee, Chang-Young Oh, Seokhwi Park, Hyunik ShinAn
improved kilogram-scale synthesis of the C1–C13 fragment
of eribulin is disclosed. Rh-mediated 6-endo-tet cyclization of a vinyl epoxide provides a crystalline
tetrahydropyran intermediate, which was transformed to a lactol intermediate
having the bicyclic motif of the C3–C12 fragment. This intermediate
was further elaborated into the C1–C13 fragment of eribulin
following the precedent sequence of reactions.
