Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides

Won Jun Choi; Hyung Ryong Moon; Hea Ok Kim; Young Mi Ko; Hye Jin Kim; Jeong A. Lee; Kang Man Lee; Mi Kyung Yun; Dae Hong Shin; Moon Woo Chun; Yhun Y. Sheen; Kilhyoun Kim; Lak Shin Jeong

doi:10.1081/NCN-200061832

Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides

Won Jun Choi
, Hyung Ryong Moon
, Hea Ok Kim
, Young Mi Ko
, Hye Jin Kim
, Jeong A. Lee
, Kang Man Lee
, Mi Kyung Yun
, Dae Hong Shin
, Moon Woo Chun
, Yhun Y. Sheen
, Kilhyoun Kim
, Lak Shin Jeong

Department of Pharmacy

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

1 Scopus citations

Abstract

The preparative and stereoselective synthesis (45-50% overall yields, >50 g scale) of the key carbasugars 7a-d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions.

Original language	English
Pages (from-to)	611-613
Number of pages	3
Journal	Nucleosides, Nucleotides and Nucleic Acids
Volume	24
Issue number	5-7
DOIs	https://doi.org/10.1081/NCN-200061832
State	Published - 2005

Keywords

3-Hydroxymethyl-D-cyclopentenone
Carbocyclic Nucleosides

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10.1081/NCN-200061832

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Choi, W. J., Moon, H. R., Kim, H. O., Ko, Y. M., Kim, H. J., Lee, J. A., Lee, K. M., Yun, M. K., Shin, D. H., Chun, M. W., Sheen, Y. Y., Kim, K., & Jeong, L. S. (2005). Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides. Nucleosides, Nucleotides and Nucleic Acids, 24(5-7), 611-613. https://doi.org/10.1081/NCN-200061832

@article{df51b32450834053bff97a95a90c7833,

title = "Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides",

abstract = "The preparative and stereoselective synthesis (45-50\% overall yields, >50 g scale) of the key carbasugars 7a-d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions.",

keywords = "3-Hydroxymethyl-D-cyclopentenone, Carbocyclic Nucleosides",

author = "Choi, \{Won Jun\} and Moon, \{Hyung Ryong\} and Kim, \{Hea Ok\} and Ko, \{Young Mi\} and Kim, \{Hye Jin\} and Lee, \{Jeong A.\} and Lee, \{Kang Man\} and Yun, \{Mi Kyung\} and Shin, \{Dae Hong\} and Chun, \{Moon Woo\} and Sheen, \{Yhun Y.\} and Kilhyoun Kim and Jeong, \{Lak Shin\}",

year = "2005",

doi = "10.1081/NCN-200061832",

language = "English",

volume = "24",

pages = "611--613",

journal = "Nucleosides, Nucleotides and Nucleic Acids",

issn = "1525-7770",

publisher = "Taylor and Francis Ltd.",

number = "5-7",

}

Choi, WJ, Moon, HR, Kim, HO, Ko, YM, Kim, HJ, Lee, JA, Lee, KM, Yun, MK, Shin, DH, Chun, MW, Sheen, YY, Kim, K & Jeong, LS 2005, 'Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides', Nucleosides, Nucleotides and Nucleic Acids, vol. 24, no. 5-7, pp. 611-613. https://doi.org/10.1081/NCN-200061832

TY - JOUR

T1 - Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides

AU - Choi, Won Jun

AU - Moon, Hyung Ryong

AU - Kim, Hea Ok

AU - Ko, Young Mi

AU - Kim, Hye Jin

AU - Lee, Jeong A.

AU - Lee, Kang Man

AU - Yun, Mi Kyung

AU - Shin, Dae Hong

AU - Chun, Moon Woo

AU - Sheen, Yhun Y.

AU - Kim, Kilhyoun

AU - Jeong, Lak Shin

PY - 2005

Y1 - 2005

N2 - The preparative and stereoselective synthesis (45-50% overall yields, >50 g scale) of the key carbasugars 7a-d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions.

AB - The preparative and stereoselective synthesis (45-50% overall yields, >50 g scale) of the key carbasugars 7a-d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions.

KW - 3-Hydroxymethyl-D-cyclopentenone

KW - Carbocyclic Nucleosides

UR - https://www.scopus.com/pages/publications/26644475882

U2 - 10.1081/NCN-200061832

DO - 10.1081/NCN-200061832

M3 - Article

C2 - 16247998

AN - SCOPUS:26644475882

SN - 1525-7770

VL - 24

SP - 611

EP - 613

JO - Nucleosides, Nucleotides and Nucleic Acids

JF - Nucleosides, Nucleotides and Nucleic Acids

IS - 5-7

ER -

Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides

Abstract

Keywords

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