Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides: Effects of the Bulky Protecting Groups to Enforce Facial Selectivity
Title
Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides: Effects of the Bulky Protecting Groups to Enforce Facial Selectivity
Journal of Organic Chemistry vol. 69, no. 7, pp. 2634 - 2636
Indexed
SCI; SCIE; SCOPUS
Document Type
Article
Abstract
The preparative and stereoselective synthesis (45-50% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the tertiary β-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.