Concise synthesis of the anti-HIV nucleoside EFdA

Masayuki Kageyama; Takuho Miyagi; Mayumi Yoshida; Tomohiro Nagasawa; Hiroshi Ohrui; Shigefumi Kuwahara

doi:10.1271/bbb.120134

Concise synthesis of the anti-HIV nucleoside EFdA

Masayuki Kageyama, Takuho Miyagi, Mayumi Yoshida, Tomohiro Nagasawa, Hiroshi Ohrui, Shigefumi Kuwahara

AGR - Bioscience and Biotechnology for Future Bioindustries

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

11 Citations (Scopus)

Abstract

EFdA (4'-ethynyl-2-fluoro-2'-deoxyadenosine), a nucleoside reverse transcriptase inhibitor with extremely potent anti-HIV activity, was concisely synthesized from (R)-glyceraldehyde acetonide in an 18% overall yield by a 12-step sequence involving highly diastereoselective ethynylation of an α-alkoxy ketone intermediate. The present synthesis is superior, both in overall yield and in the number of steps, to the previous one which required 18 steps from an expensive starting material and resulted in a modest overall yield of 2.5%.

Original language	English
Pages (from-to)	1219-1225
Number of pages	7
Journal	Bioscience, Biotechnology and Biochemistry
Volume	76
Issue number	6
DOIs	https://doi.org/10.1271/bbb.120134
Publication status	Published - 2012

Keywords

AIDS
Anti-HIV
EFdA
N-glycosidation
Nucleoside

ASJC Scopus subject areas

Biotechnology
Analytical Chemistry
Biochemistry
Applied Microbiology and Biotechnology
Molecular Biology
Organic Chemistry

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title = "Concise synthesis of the anti-HIV nucleoside EFdA",

abstract = "EFdA (4'-ethynyl-2-fluoro-2'-deoxyadenosine), a nucleoside reverse transcriptase inhibitor with extremely potent anti-HIV activity, was concisely synthesized from (R)-glyceraldehyde acetonide in an 18% overall yield by a 12-step sequence involving highly diastereoselective ethynylation of an α-alkoxy ketone intermediate. The present synthesis is superior, both in overall yield and in the number of steps, to the previous one which required 18 steps from an expensive starting material and resulted in a modest overall yield of 2.5%.",

keywords = "AIDS, Anti-HIV, EFdA, N-glycosidation, Nucleoside",

author = "Masayuki Kageyama and Takuho Miyagi and Mayumi Yoshida and Tomohiro Nagasawa and Hiroshi Ohrui and Shigefumi Kuwahara",

note = "Funding Information: This work was supported, in part, by a grant aid for scientific research (B) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (no. 19380065). We thank Ms. Yamada (Tohoku University) for measuring the NMR and MS spectra.",

year = "2012",

doi = "10.1271/bbb.120134",

language = "English",

volume = "76",

pages = "1219--1225",

journal = "Bioscience, Biotechnology and Biochemistry",

issn = "0916-8451",

publisher = "Japan Society for Bioscience Biotechnology and Agrochemistry",

number = "6",

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T1 - Concise synthesis of the anti-HIV nucleoside EFdA

AU - Kageyama, Masayuki

AU - Miyagi, Takuho

AU - Yoshida, Mayumi

AU - Nagasawa, Tomohiro

AU - Ohrui, Hiroshi

AU - Kuwahara, Shigefumi

N1 - Funding Information: This work was supported, in part, by a grant aid for scientific research (B) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (no. 19380065). We thank Ms. Yamada (Tohoku University) for measuring the NMR and MS spectra.

PY - 2012

Y1 - 2012

N2 - EFdA (4'-ethynyl-2-fluoro-2'-deoxyadenosine), a nucleoside reverse transcriptase inhibitor with extremely potent anti-HIV activity, was concisely synthesized from (R)-glyceraldehyde acetonide in an 18% overall yield by a 12-step sequence involving highly diastereoselective ethynylation of an α-alkoxy ketone intermediate. The present synthesis is superior, both in overall yield and in the number of steps, to the previous one which required 18 steps from an expensive starting material and resulted in a modest overall yield of 2.5%.

AB - EFdA (4'-ethynyl-2-fluoro-2'-deoxyadenosine), a nucleoside reverse transcriptase inhibitor with extremely potent anti-HIV activity, was concisely synthesized from (R)-glyceraldehyde acetonide in an 18% overall yield by a 12-step sequence involving highly diastereoselective ethynylation of an α-alkoxy ketone intermediate. The present synthesis is superior, both in overall yield and in the number of steps, to the previous one which required 18 steps from an expensive starting material and resulted in a modest overall yield of 2.5%.

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KW - Anti-HIV

KW - EFdA

KW - N-glycosidation

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