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

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

Department of Pharmacy

Ewha Womans University

Research output: Contribution to journal › Article › peer-review

85 Scopus citations

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.

Original language	English
Pages (from-to)	2634-2636
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	69
Issue number	7
DOIs	https://doi.org/10.1021/jo0356762
State	Published - 2 Apr 2004

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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.",

author = "Choi, {Won Jun} and Moon, {Hyung Ryong} and Kim, {Hea Ok} and Yoo, {Byul Nae} and Lee, {Jeong A.} and Shin, {Dae Hong} and Jeong, {Lak Shin}",

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AU - Choi, Won Jun

AU - Moon, Hyung Ryong

AU - Kim, Hea Ok

AU - Yoo, Byul Nae

AU - Lee, Jeong A.

AU - Shin, Dae Hong

AU - Jeong, Lak Shin

PY - 2004/4/2

Y1 - 2004/4/2

N2 - 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.

AB - 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.

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Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides: Effects of the Bulky Protecting Groups to Enforce Facial Selectivity

Abstract

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