Open AccessTotal and formal syntheses of fostriecin
Author(s) -
Dong Gao,
Bohui Li,
George A. O’Doherty
Publication year - 2020
Publication title -
organic chemistry frontiers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.377
H-Index - 56
eISSN - 2052-4129
pISSN - 2052-4110
DOI - 10.1039/d0qo01121e
Subject(s) - chemistry , dihydroxylation , total synthesis , stereochemistry , sharpless asymmetric dihydroxylation , hydroboration , formal synthesis , natural product , alkyne , enantioselective synthesis , organic chemistry , catalysis
Two formal syntheses and one total synthesis of fostriecin ( 1 ) have been achieved, as well as, the synthesis of its related congener dihydro-dephospho-fostriecin. All the routes use the Sharpless dihydroxylation to set the absolute stereochemistry at C -8/9 positions and a Leighton allylation to set the C -5 position of the natural product. In the formal syntheses a Noyori transfer hydrogenation of an ynone was used to set the C -11 position while the total synthesis employed a combination of asymmetric dihydroxylation and Pd-π-allyl reduction to set the C -11 position. Finally in the total synthesis, a trans-hydroboration of the C -12/13 alkyne was used in combination with a Suzuki cross coupling to establish the Z , Z , E -triene of fostriecin ( 1 ).