Enantioselective total synthesis of the potent Anti-HIV nucleoside EFdA

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

doi:10.1021/ol202116k

Enantioselective total synthesis of the potent Anti-HIV nucleoside EFdA

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

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

27 Citations (Scopus)

Abstract

A concise enantioselective total synthesis of 4′-ethynyl-2-fluoro- 2′-deoxyadenosine (EFdA), an extremely potent anti-HIV agent, has been accomplished from (R)-glyceraldehyde acetonide in 18% overall yield by a 12-step sequence involving a highly diastereoselective ethynylation of an α-alkoxy ketone intermediate

Original language	English
Pages (from-to)	5264-5266
Number of pages	3
Journal	Organic letters
Volume	13
Issue number	19
DOIs	https://doi.org/10.1021/ol202116k
Publication status	Published - 2011 Oct 7

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

UN SDGs

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

Access to Document

10.1021/ol202116k

Cite this

@article{731ed33ae6a14714aa27962da06b3c38,

title = "Enantioselective total synthesis of the potent Anti-HIV nucleoside EFdA",

abstract = "A concise enantioselective total synthesis of 4′-ethynyl-2-fluoro- 2′-deoxyadenosine (EFdA), an extremely potent anti-HIV agent, has been accomplished from (R)-glyceraldehyde acetonide in 18% overall yield by a 12-step sequence involving a highly diastereoselective ethynylation of an α-alkoxy ketone intermediate",

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

year = "2011",

month = oct,

day = "7",

doi = "10.1021/ol202116k",

language = "English",

volume = "13",

pages = "5264--5266",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Enantioselective total synthesis of the potent Anti-HIV nucleoside EFdA

AU - Kageyama, Masayuki

AU - Nagasawa, Tomohiro

AU - Yoshida, Mayumi

AU - Ohrui, Hiroshi

AU - Kuwahara, Shigefumi

PY - 2011/10/7

Y1 - 2011/10/7

N2 - A concise enantioselective total synthesis of 4′-ethynyl-2-fluoro- 2′-deoxyadenosine (EFdA), an extremely potent anti-HIV agent, has been accomplished from (R)-glyceraldehyde acetonide in 18% overall yield by a 12-step sequence involving a highly diastereoselective ethynylation of an α-alkoxy ketone intermediate

AB - A concise enantioselective total synthesis of 4′-ethynyl-2-fluoro- 2′-deoxyadenosine (EFdA), an extremely potent anti-HIV agent, has been accomplished from (R)-glyceraldehyde acetonide in 18% overall yield by a 12-step sequence involving a highly diastereoselective ethynylation of an α-alkoxy ketone intermediate

UR - http://www.scopus.com/inward/record.url?scp=80054745392&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80054745392&partnerID=8YFLogxK

U2 - 10.1021/ol202116k

DO - 10.1021/ol202116k

M3 - Article

C2 - 21888325

AN - SCOPUS:80054745392

SN - 1523-7060

VL - 13

SP - 5264

EP - 5266

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Enantioselective total synthesis of the potent Anti-HIV nucleoside EFdA

Abstract

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this