Concise entry to chiral 5-(4-Hydroxybutyl)-2(5 H)-furanone via HTIB-mediated novel oxidative fragmentation: Formal total synthesis of (+)-dubiusamine A

Muneo Kawasumi; Yoshiharu Iwabuchi

doi:10.1021/ol4005239

Concise entry to chiral 5-(4-Hydroxybutyl)-2(5 H)-furanone via HTIB-mediated novel oxidative fragmentation: Formal total synthesis of (+)-dubiusamine A

Muneo Kawasumi, Yoshiharu Iwabuchi

PHA - Molecular Pharmaceutical Science

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

13 Citations (Scopus)

Abstract

The concise synthesis of 5-(4-hydroxybutyl)-2(5H)furanone has been accomplished from 9-oxabicyclo[4.2.1]non-7-en-1-ol on the basis of HTIB [PhI(OH)OTs, a.k.a. Koser's reagent]-mediated novel oxidative fragmentation. Chiral (-)-(R)-5-(4-hydroxy-butyl)-2(5H)-furanone (>99% ee) was used for the formal total synthesis of (+)-dubiusamine A (1).

Original language	English
Pages (from-to)	1788-1790
Number of pages	3
Journal	Organic letters
Volume	15
Issue number	7
DOIs	https://doi.org/10.1021/ol4005239
Publication status	Published - 2013 Apr 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Concise entry to chiral 5-(4-Hydroxybutyl)-2(5 H)-furanone via HTIB-mediated novel oxidative fragmentation: Formal total synthesis of (+)-dubiusamine A",

abstract = "The concise synthesis of 5-(4-hydroxybutyl)-2(5H)furanone has been accomplished from 9-oxabicyclo[4.2.1]non-7-en-1-ol on the basis of HTIB [PhI(OH)OTs, a.k.a. Koser's reagent]-mediated novel oxidative fragmentation. Chiral (-)-(R)-5-(4-hydroxy-butyl)-2(5H)-furanone (>99% ee) was used for the formal total synthesis of (+)-dubiusamine A (1).",

author = "Muneo Kawasumi and Yoshiharu Iwabuchi",

year = "2013",

month = apr,

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doi = "10.1021/ol4005239",

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journal = "Organic Letters",

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T2 - Formal total synthesis of (+)-dubiusamine A

AU - Kawasumi, Muneo

AU - Iwabuchi, Yoshiharu

PY - 2013/4/5

Y1 - 2013/4/5

N2 - The concise synthesis of 5-(4-hydroxybutyl)-2(5H)furanone has been accomplished from 9-oxabicyclo[4.2.1]non-7-en-1-ol on the basis of HTIB [PhI(OH)OTs, a.k.a. Koser's reagent]-mediated novel oxidative fragmentation. Chiral (-)-(R)-5-(4-hydroxy-butyl)-2(5H)-furanone (>99% ee) was used for the formal total synthesis of (+)-dubiusamine A (1).

AB - The concise synthesis of 5-(4-hydroxybutyl)-2(5H)furanone has been accomplished from 9-oxabicyclo[4.2.1]non-7-en-1-ol on the basis of HTIB [PhI(OH)OTs, a.k.a. Koser's reagent]-mediated novel oxidative fragmentation. Chiral (-)-(R)-5-(4-hydroxy-butyl)-2(5H)-furanone (>99% ee) was used for the formal total synthesis of (+)-dubiusamine A (1).

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Concise entry to chiral 5-(4-Hydroxybutyl)-2(5 H)-furanone via HTIB-mediated novel oxidative fragmentation: Formal total synthesis of (+)-dubiusamine A

Abstract

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