Redox refunctionalization of steroid spiroketals. Structure correction of ritterazine M.
The structure of the North spiroketal moiety of ritterazine M has been corrected from 1a to 1b. This was accomplished by comparison of published spectra of the natural product with five synthetic spiroketal-alcohols. Synthesis of these models was efficiently accomplished by reductive cleavage of the spiroketal and Sharpless asymmetric dihydroxylation of an isopentyl, methyl 1,1-disubstituted olefin, followed by Suarez iodine[III] oxidative spirocyclization of monoprotected 1 degree,3 degree 1,2 diols.
Lee
Seongmin
S
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
LaCour
Thomas G
TG
Lantrip
Douglas
D
Fuchs
Philip L
PL
D015394:Molecular Structure; D010084:Oxidation-Reduction; D010619:Phenazines; D013141:Spiro Compounds / Q000737:chemistry*; D013256:Steroids / Q000737:chemistry*
D010619:Phenazines; D013141:Spiro Compounds; D013256:Steroids; C448328:ritterazine M