Synthesis of 3′-deoxyribolactones using a hydrolysis-induced lactonization cascade reaction of epoxy cyanohydrins

Danielle J. Vugts; Halil Aktas; Kanar Al-Mafraji; Frans J.J. De Kanter; Eelco Ruijter; Marinus B. Groen; Romano V.A. Orru

doi:https://doi.org/10.1002/ejoc.200701152

Synthesis of 3′-deoxyribolactones using a hydrolysis-induced lactonization cascade reaction of epoxy cyanohydrins

Danielle J. Vugts, Halil Aktas, Kanar Al-Mafraji, Frans J.J. De Kanter, Eelco Ruijter, Marinus B. Groen, Romano V.A. Orru

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

5 Citations (Scopus)

Abstract

The synthesis of 3′-deoxyribolactones was accomplished in a few steps from the commercially available 3-decyn-1-ol in 44% overall yield. The key transformation comprises a one-pot four-reaction hydrolysis-induced lactonization cascade. The strategy was employed to efficiently access optically active 5′-chloro-3′-deoxyribolactones.

Original language	English
Pages (from-to)	1336-1339
Number of pages	4
Journal	European Journal of Organic Chemistry
Issue number	8
DOIs	https://doi.org/10.1002/ejoc.200701152
Publication status	Published - Mar 2008
Externally published	Yes

Keywords

3-Deoxyribolactone
Cascade reaction
Cyanohydrin
Cyclization

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https://doi.org/10.1002/ejoc.200701152

Cite this

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title = "Synthesis of 3′-deoxyribolactones using a hydrolysis-induced lactonization cascade reaction of epoxy cyanohydrins",

abstract = "The synthesis of 3′-deoxyribolactones was accomplished in a few steps from the commercially available 3-decyn-1-ol in 44% overall yield. The key transformation comprises a one-pot four-reaction hydrolysis-induced lactonization cascade. The strategy was employed to efficiently access optically active 5′-chloro-3′-deoxyribolactones.",

keywords = "3-Deoxyribolactone, Cascade reaction, Cyanohydrin, Cyclization",

author = "Vugts, {Danielle J.} and Halil Aktas and Kanar Al-Mafraji and {De Kanter}, {Frans J.J.} and Eelco Ruijter and Groen, {Marinus B.} and Orru, {Romano V.A.}",

year = "2008",

month = mar,

doi = "https://doi.org/10.1002/ejoc.200701152",

language = "English",

pages = "1336--1339",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - Synthesis of 3′-deoxyribolactones using a hydrolysis-induced lactonization cascade reaction of epoxy cyanohydrins

AU - Vugts, Danielle J.

AU - Aktas, Halil

AU - Al-Mafraji, Kanar

AU - De Kanter, Frans J.J.

AU - Ruijter, Eelco

AU - Groen, Marinus B.

AU - Orru, Romano V.A.

PY - 2008/3

Y1 - 2008/3

N2 - The synthesis of 3′-deoxyribolactones was accomplished in a few steps from the commercially available 3-decyn-1-ol in 44% overall yield. The key transformation comprises a one-pot four-reaction hydrolysis-induced lactonization cascade. The strategy was employed to efficiently access optically active 5′-chloro-3′-deoxyribolactones.

AB - The synthesis of 3′-deoxyribolactones was accomplished in a few steps from the commercially available 3-decyn-1-ol in 44% overall yield. The key transformation comprises a one-pot four-reaction hydrolysis-induced lactonization cascade. The strategy was employed to efficiently access optically active 5′-chloro-3′-deoxyribolactones.

KW - 3-Deoxyribolactone

KW - Cascade reaction

KW - Cyanohydrin

KW - Cyclization

UR - http://www.scopus.com/inward/record.url?scp=53849126536&partnerID=8YFLogxK

U2 - https://doi.org/10.1002/ejoc.200701152

DO - https://doi.org/10.1002/ejoc.200701152

M3 - Article

SN - 1434-193X

SP - 1336

EP - 1339

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 8

ER -

Synthesis of 3′-deoxyribolactones using a hydrolysis-induced lactonization cascade reaction of epoxy cyanohydrins

Abstract

Keywords

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