Stereoselective Total Synthesis of Siladenoserinols A and D
Yinxin Liu, Jun Liu, Chuanfang Zhao, Yuguo Du
Abstract
The stereoselective total synthesis of siladenoserinols A and D has been accomplished using carbohydrate as a chiral template. The feature of this work is to build the medicinally privileged 6,8-DOBCO scaffold through a cascade reaction of hydrogenation/deacetalization/ketalization in a one-pot process, that is, to take advantage of a thermodynamically controlled bicyclization of polyhydroxyketone under HCl/MeOH reaction conditions. The current cost-effective synthetic strategy could facilitate the bioactivity investigation of siladenoserinols.
Topics & Concepts
StereoselectivityChemistryCombinatorial chemistryCascadeTotal synthesisReaction conditionsOrganic chemistryCatalysisChromatographySynthetic Organic Chemistry MethodsCarbohydrate Chemistry and SynthesisEnzyme function and inhibition