Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions

RAJEEV SHRIVASTAVA; Elise  Maudru; Gurdial Singh; Richard H.  Wightman; Keith M.  Morgan

doi:doi:10.3762/bjoc.4.43

Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions

RAJEEV SHRIVASTAVA, Elise Maudru, Gurdial Singh^*, Richard H. Wightman, Keith M. Morgan

^*Corresponding author for this work

Biology

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

6 Citations (Scopus)

Abstract

Treatment of 5-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribose with lithium acetylides gave mixtures of syn- and antialkynols 2a–2c which were separated following protection as methoxymethyl ethers. These were converted to the corresponding
iodides which underwent 6-exo-dig radical cyclisation to afford chiral cyclohexanes and carbasugars. Oxidation of the primary
alcohols 6a–b gave the corresponding aldehydes which on treatment with Grignard reagents afforded a mixture of alcohols. The
corresponding iodides underwent similar 6-exo-dig cyclisation to give fully functionalised cyclohexanes

Original language	English
Number of pages	8
Journal	Beilstein Journal of Organic Chemistry
Volume	4
Issue number	43
DOIs	https://doi.org/doi:10.3762/bjoc.4.43
Publication status	Published - 19 Nov 2008

Keywords

carbasugars; cyclisation; cyclohexanes; 6-membered ring; stereoisomers

Access to Document

doi:10.3762/bjoc.4.43Licence: Other

Cite this

@article{f0b50271bd1e470c8a597da610e76d2a,

title = "Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions",

abstract = "Treatment of 5-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribose with lithium acetylides gave mixtures of syn- and antialkynols 2a–2c which were separated following protection as methoxymethyl ethers. These were converted to the correspondingiodides which underwent 6-exo-dig radical cyclisation to afford chiral cyclohexanes and carbasugars. Oxidation of the primaryalcohols 6a–b gave the corresponding aldehydes which on treatment with Grignard reagents afforded a mixture of alcohols. Thecorresponding iodides underwent similar 6-exo-dig cyclisation to give fully functionalised cyclohexanes",

keywords = "carbasugars; cyclisation; cyclohexanes; 6-membered ring; stereoisomers",

author = "RAJEEV SHRIVASTAVA and Elise Maudru and Gurdial Singh and Wightman, {Richard H.} and Morgan, {Keith M.}",

year = "2008",

month = nov,

day = "19",

doi = "doi:10.3762/bjoc.4.43",

language = "English",

volume = "4",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

number = "43",

}

TY - JOUR

T1 - Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions

AU - SHRIVASTAVA, RAJEEV

AU - Maudru, Elise

AU - Singh, Gurdial

AU - Wightman, Richard H.

AU - Morgan, Keith M.

PY - 2008/11/19

Y1 - 2008/11/19

N2 - Treatment of 5-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribose with lithium acetylides gave mixtures of syn- and antialkynols 2a–2c which were separated following protection as methoxymethyl ethers. These were converted to the correspondingiodides which underwent 6-exo-dig radical cyclisation to afford chiral cyclohexanes and carbasugars. Oxidation of the primaryalcohols 6a–b gave the corresponding aldehydes which on treatment with Grignard reagents afforded a mixture of alcohols. Thecorresponding iodides underwent similar 6-exo-dig cyclisation to give fully functionalised cyclohexanes

AB - Treatment of 5-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribose with lithium acetylides gave mixtures of syn- and antialkynols 2a–2c which were separated following protection as methoxymethyl ethers. These were converted to the correspondingiodides which underwent 6-exo-dig radical cyclisation to afford chiral cyclohexanes and carbasugars. Oxidation of the primaryalcohols 6a–b gave the corresponding aldehydes which on treatment with Grignard reagents afforded a mixture of alcohols. Thecorresponding iodides underwent similar 6-exo-dig cyclisation to give fully functionalised cyclohexanes

KW - carbasugars; cyclisation; cyclohexanes; 6-membered ring; stereoisomers

U2 - doi:10.3762/bjoc.4.43

DO - doi:10.3762/bjoc.4.43

M3 - Article (journal)

SN - 1860-5397

VL - 4

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

IS - 43

ER -

Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions

Abstract

Keywords

Access to Document

Fingerprint

Cite this