Synthesis of EFdA via a diastereoselective aldol reaction of a protected 3-keto furanose

Kei Fukuyama; Hiroshi Ohrui; Shigefumi Kuwahara

doi:10.1021/ol5036535

Synthesis of EFdA via a diastereoselective aldol reaction of a protected 3-keto furanose

Kei Fukuyama, Hiroshi Ohrui, Shigefumi Kuwahara

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

22 Citations (Scopus)

Abstract

An efficient enantioselective total synthesis of EFdA, a remarkably potent anti-HIV nucleoside analogue with various favorable pharmacological profiles, has been achieved in 37% overall yield from diacetone-d-glucose by a 14-step sequence that features a highly diastereoselective installation of the tetrasubstituted stereogenic center at the C4′ position, direct oxidative cleavage of an acetonide-protected diol derivative to an aldehyde, and one-pot 2′-deoxygenation of a ribonucleoside intermediate.

Original language	English
Pages (from-to)	828-831
Number of pages	4
Journal	Organic letters
Volume	17
Issue number	4
DOIs	https://doi.org/10.1021/ol5036535
Publication status	Published - 2015 Feb 20

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol5036535

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abstract = "An efficient enantioselective total synthesis of EFdA, a remarkably potent anti-HIV nucleoside analogue with various favorable pharmacological profiles, has been achieved in 37% overall yield from diacetone-d-glucose by a 14-step sequence that features a highly diastereoselective installation of the tetrasubstituted stereogenic center at the C4′ position, direct oxidative cleavage of an acetonide-protected diol derivative to an aldehyde, and one-pot 2′-deoxygenation of a ribonucleoside intermediate.",

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Synthesis of EFdA via a diastereoselective aldol reaction of a protected 3-keto furanose

Abstract

ASJC Scopus subject areas

UN SDGs

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