Open AccessA Convergent Total Synthesis of the Potent Cephalostatin/Ritterazine Hybrid -25-epi Ritterostatin GN1N
Author(s) -
Ananda Kumar Kanduluru,
Prabal Banerjee,
John A. Beutler,
P. L. Fuchs
Publication year - 2013
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/jo401171q
Subject(s) - chemistry , stereocenter , dihydroxylation , azide , stereochemistry , stereoselectivity , convergent synthesis , sharpless asymmetric dihydroxylation , ligand (biochemistry) , total synthesis , combinatorial chemistry , enantioselective synthesis , organic chemistry , receptor , biochemistry , catalysis
The convergent synthesis of 25-epi ritterostatin GN1N is described for the first time, starting from hecogenin acetate (HA). Stereoselective dihydroxylation employing the chiral ligand (DHQ)2PHAL was used as the key step to introduce the C25 epi-stereocenter on the north 1 segment. The title compound was obtained through a coupling reaction between the C3-keto-azide (cstat North 1) and North G.