Synthesis of D- and L-apio nucleoside analogues with 2′-hydroxyl group as potential anti-HIV agents

Dong Zhe Jin; Sung Hee Kwon; Hyung Ryong Moon; Prashantha Gunaga; Hea Ok Kim; Dae Kee Kim; Moon Woo Chun; Lak Shin Jeong

doi:10.1016/j.bmc.2003.12.002

Synthesis of D- and L-apio nucleoside analogues with 2′-hydroxyl group as potential anti-HIV agents

Dong Zhe Jin
, Sung Hee Kwon
, Hyung Ryong Moon
, Prashantha Gunaga
, Hea Ok Kim
, Dae Kee Kim
, Moon Woo Chun
, Lak Shin Jeong

Department of Pharmaceutical Sciences

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

15 Scopus citations

Abstract

The present work describes the asymmetric synthesis of D- and L-apio-2′,3′-dideoxynucleoside analogues, 4 and 5 with 2′-hydroxyl group via a common intermediate 9, starting from D-galactose. Stereoselective dihydroxylation and deoxygenation through radical inversion were successfully employed to synthesize the key intermediate 12 with D-apio structure, while stereoselecetive hydroboration-oxidation was used for the synthesis of another key intermediate 18 with L-apio structure.

Original language	English
Pages (from-to)	1101-1109
Number of pages	9
Journal	Bioorganic and Medicinal Chemistry
Volume	12
Issue number	5
DOIs	https://doi.org/10.1016/j.bmc.2003.12.002
State	Published - 1 Mar 2004

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Antiviral
Apio nucleotides
Stereoselective

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10.1016/j.bmc.2003.12.002

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title = "Synthesis of D- and L-apio nucleoside analogues with 2′-hydroxyl group as potential anti-HIV agents",

abstract = "The present work describes the asymmetric synthesis of D- and L-apio-2′,3′-dideoxynucleoside analogues, 4 and 5 with 2′-hydroxyl group via a common intermediate 9, starting from D-galactose. Stereoselective dihydroxylation and deoxygenation through radical inversion were successfully employed to synthesize the key intermediate 12 with D-apio structure, while stereoselecetive hydroboration-oxidation was used for the synthesis of another key intermediate 18 with L-apio structure.",

keywords = "Antiviral, Apio nucleotides, Stereoselective",

author = "Jin, \{Dong Zhe\} and Kwon, \{Sung Hee\} and Moon, \{Hyung Ryong\} and Prashantha Gunaga and Kim, \{Hea Ok\} and Kim, \{Dae Kee\} and Chun, \{Moon Woo\} and Jeong, \{Lak Shin\}",

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doi = "10.1016/j.bmc.2003.12.002",

language = "English",

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journal = "Bioorganic and Medicinal Chemistry",

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T1 - Synthesis of D- and L-apio nucleoside analogues with 2′-hydroxyl group as potential anti-HIV agents

AU - Jin, Dong Zhe

AU - Kwon, Sung Hee

AU - Moon, Hyung Ryong

AU - Gunaga, Prashantha

AU - Kim, Hea Ok

AU - Kim, Dae Kee

AU - Chun, Moon Woo

AU - Jeong, Lak Shin

PY - 2004/3/1

Y1 - 2004/3/1

N2 - The present work describes the asymmetric synthesis of D- and L-apio-2′,3′-dideoxynucleoside analogues, 4 and 5 with 2′-hydroxyl group via a common intermediate 9, starting from D-galactose. Stereoselective dihydroxylation and deoxygenation through radical inversion were successfully employed to synthesize the key intermediate 12 with D-apio structure, while stereoselecetive hydroboration-oxidation was used for the synthesis of another key intermediate 18 with L-apio structure.

AB - The present work describes the asymmetric synthesis of D- and L-apio-2′,3′-dideoxynucleoside analogues, 4 and 5 with 2′-hydroxyl group via a common intermediate 9, starting from D-galactose. Stereoselective dihydroxylation and deoxygenation through radical inversion were successfully employed to synthesize the key intermediate 12 with D-apio structure, while stereoselecetive hydroboration-oxidation was used for the synthesis of another key intermediate 18 with L-apio structure.

KW - Antiviral

KW - Apio nucleotides

KW - Stereoselective

UR - https://www.scopus.com/pages/publications/1342321885

U2 - 10.1016/j.bmc.2003.12.002

DO - 10.1016/j.bmc.2003.12.002

M3 - Article

C2 - 14980622

AN - SCOPUS:1342321885

SN - 0968-0896

VL - 12

SP - 1101

EP - 1109

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 5

ER -

Synthesis of D- and L-apio nucleoside analogues with 2′-hydroxyl group as potential anti-HIV agents

Abstract

UN SDGs

Keywords

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