Synthesis of the reported structure of pogostol and a total synthesis of (±)-kessane without the use of protecting groups

Kevin I. Booker-Milburn; Helen Jenkins; Jonathan P H Charmant; Peter Mohr

doi:10.1021/ol035373u

Synthesis of the reported structure of pogostol and a total synthesis of (±)-kessane without the use of protecting groups

Kevin I. Booker-Milburn^*
, Helen Jenkins
, Jonathan P H Charmant
, Peter Mohr

^*Corresponding author for this work

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

29 Citations (Scopus)

Abstract

(Matrix presented) A short racemic synthesis of kessane from 4-hydroxy-4-methyl-2-cyclohexenone is described using a route that also resulted in the synthesis of the reported structure of pogostol. The key step involves an Fe(III)-mediated tandem radical ring-expansion/cyclization of the cyclopropylsilyl ether 9. No protecting groups are used in the entire sequence. Comparison of the NMR data of synthetic pogostol to that in the literature indicates that the structure originally proposed is incorrect.

Translated title of the contribution	Synthesis of the Reported Structure of Pogostol and a Total Synthesis of (±)-Kessane without the Use of Protecting Groups
Original language	English
Pages (from-to)	3309-3312
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	18
DOIs	https://doi.org/10.1021/ol035373u
Publication status	Published - 4 Sept 2003

Bibliographical note

Publisher: American Chemical Society

Research Groups and Themes

Inorganic & Materials

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10.1021/ol035373u

http://pubs.acs.org/cgi-bin/abstract.cgi/orlef7/2003/5/i18/abs/ol035373u.html

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title = "Synthesis of the reported structure of pogostol and a total synthesis of (±)-kessane without the use of protecting groups",

abstract = "(Matrix presented) A short racemic synthesis of kessane from 4-hydroxy-4-methyl-2-cyclohexenone is described using a route that also resulted in the synthesis of the reported structure of pogostol. The key step involves an Fe(III)-mediated tandem radical ring-expansion/cyclization of the cyclopropylsilyl ether 9. No protecting groups are used in the entire sequence. Comparison of the NMR data of synthetic pogostol to that in the literature indicates that the structure originally proposed is incorrect.",

author = "Booker-Milburn, \{Kevin I.\} and Helen Jenkins and Charmant, \{Jonathan P H\} and Peter Mohr",

note = "Publisher: American Chemical Society",

year = "2003",

month = sep,

day = "4",

doi = "10.1021/ol035373u",

language = "English",

volume = "5",

pages = "3309--3312",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Synthesis of the reported structure of pogostol and a total synthesis of (±)-kessane without the use of protecting groups

AU - Booker-Milburn, Kevin I.

AU - Jenkins, Helen

AU - Charmant, Jonathan P H

AU - Mohr, Peter

N1 - Publisher: American Chemical Society

PY - 2003/9/4

Y1 - 2003/9/4

N2 - (Matrix presented) A short racemic synthesis of kessane from 4-hydroxy-4-methyl-2-cyclohexenone is described using a route that also resulted in the synthesis of the reported structure of pogostol. The key step involves an Fe(III)-mediated tandem radical ring-expansion/cyclization of the cyclopropylsilyl ether 9. No protecting groups are used in the entire sequence. Comparison of the NMR data of synthetic pogostol to that in the literature indicates that the structure originally proposed is incorrect.

AB - (Matrix presented) A short racemic synthesis of kessane from 4-hydroxy-4-methyl-2-cyclohexenone is described using a route that also resulted in the synthesis of the reported structure of pogostol. The key step involves an Fe(III)-mediated tandem radical ring-expansion/cyclization of the cyclopropylsilyl ether 9. No protecting groups are used in the entire sequence. Comparison of the NMR data of synthetic pogostol to that in the literature indicates that the structure originally proposed is incorrect.

U2 - 10.1021/ol035373u

DO - 10.1021/ol035373u

M3 - Article (Academic Journal)

SN - 1523-7052

VL - 5

SP - 3309

EP - 3312

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Synthesis of the reported structure of pogostol and a total synthesis of (±)-kessane without the use of protecting groups

Abstract

Bibliographical note

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