Preparative and stereoselective synthesis of the versatile intermediate for carbocyclic nucleosides: effects of the bulky protecting groups to enforce facial selectivity

Won Jun Choi; Hyung Ryong Moon; Hea Ok Kim; Byul Nae Yoo; Jeong A Lee; Dae Hong Shin; Lak Shin Jeong

doi:10.1021/jo0356762

Preparative and stereoselective synthesis of the versatile intermediate for carbocyclic nucleosides: effects of the bulky protecting groups to enforce facial selectivity

J Org Chem. 2004 Apr 2;69(7):2634-6. doi: 10.1021/jo0356762.

Authors

Won Jun Choi¹, Hyung Ryong Moon, Hea Ok Kim, Byul Nae Yoo, Jeong A Lee, Dae Hong Shin, Lak Shin Jeong

Affiliation

¹ Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea.

PMID: 15049678
DOI: 10.1021/jo0356762

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 beta-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adenosine / analogs & derivatives
Adenosine / chemistry
Catalysis
Chemistry, Organic / methods*
Molecular Structure
Nucleosides / analysis
Nucleosides / chemical synthesis*
Oxidation-Reduction
Ribose / chemistry*
Stereoisomerism
Structure-Activity Relationship

Substances

Nucleosides
Ribose
neplanocin A
Adenosine