Synthesis of 1,10-dimethylbicyclo[8.8.8]hexacosane and 1,10- dihydroxybicyclo[8.8.8]hexacosane

Ian W. Jones; Yasunari Monguchi; Alice Dawson; Michael D. Carducci; Eugene A. Mash

doi:10.1021/ol050714k

Synthesis of 1,10-dimethylbicyclo[8.8.8]hexacosane and 1,10- dihydroxybicyclo[8.8.8]hexacosane

Ian W. Jones, Yasunari Monguchi, Alice Dawson, Michael D. Carducci, Eugene A. Mash

Chemistry and Biochemistry

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

6 Scopus citations

Abstract

(Chemical Equation Presented) 1,10-Dimethylbicyclo[8.8.8]hexacosane (1) and 1,10-dihydroxybicyclo[8.8.8]hexacosane (2) were prepared in 4% yield over seven steps and in 18% yield over three steps, respectively, starting from 1,10-cyclooctadecanedione. The identities and out,out conformations of these compounds were established by single-crystal X-ray analysis.

Original language	English (US)
Pages (from-to)	2841-2843
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	14
DOIs	https://doi.org/10.1021/ol050714k
State	Published - Jul 7 2005

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of 1,10-dimethylbicyclo[8.8.8]hexacosane and 1,10- dihydroxybicyclo[8.8.8]hexacosane",

abstract = "(Chemical Equation Presented) 1,10-Dimethylbicyclo[8.8.8]hexacosane (1) and 1,10-dihydroxybicyclo[8.8.8]hexacosane (2) were prepared in 4% yield over seven steps and in 18% yield over three steps, respectively, starting from 1,10-cyclooctadecanedione. The identities and out,out conformations of these compounds were established by single-crystal X-ray analysis.",

author = "Jones, {Ian W.} and Yasunari Monguchi and Alice Dawson and Carducci, {Michael D.} and Mash, {Eugene A.}",

year = "2005",

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T1 - Synthesis of 1,10-dimethylbicyclo[8.8.8]hexacosane and 1,10- dihydroxybicyclo[8.8.8]hexacosane

AU - Jones, Ian W.

AU - Monguchi, Yasunari

AU - Dawson, Alice

AU - Carducci, Michael D.

AU - Mash, Eugene A.

PY - 2005/7/7

Y1 - 2005/7/7

N2 - (Chemical Equation Presented) 1,10-Dimethylbicyclo[8.8.8]hexacosane (1) and 1,10-dihydroxybicyclo[8.8.8]hexacosane (2) were prepared in 4% yield over seven steps and in 18% yield over three steps, respectively, starting from 1,10-cyclooctadecanedione. The identities and out,out conformations of these compounds were established by single-crystal X-ray analysis.

AB - (Chemical Equation Presented) 1,10-Dimethylbicyclo[8.8.8]hexacosane (1) and 1,10-dihydroxybicyclo[8.8.8]hexacosane (2) were prepared in 4% yield over seven steps and in 18% yield over three steps, respectively, starting from 1,10-cyclooctadecanedione. The identities and out,out conformations of these compounds were established by single-crystal X-ray analysis.

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Synthesis of 1,10-dimethylbicyclo[8.8.8]hexacosane and 1,10- dihydroxybicyclo[8.8.8]hexacosane

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