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

13 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

Keywords

Antiviral
Apio nucleotides
Stereoselective

UN SDGs

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

Access to Document

10.1016/j.bmc.2003.12.002

Cite this

@article{1563c8a2fd56496096f0dfa99f08f9c3,

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}",

year = "2004",

month = mar,

day = "1",

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

language = "English",

volume = "12",

pages = "1101--1109",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Ltd.",

number = "5",

}

TY - JOUR

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 - http://www.scopus.com/inward/record.url?scp=1342321885&partnerID=8YFLogxK

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

Keywords

UN SDGs

Access to Document

Fingerprint

Cite this