Tetrahedron

, volume 59 , issue 40 , pages 7949-7960

Use of epoxidation and epoxide opening reactions for the synthesis of highly functionalized 1-oxaspiro[4.5]decan-2-ones and related compounds

Martin Eipert ¹

Cäcilia Maichle-Mössmer ²

M. E. Maier ¹

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Institut für Organische Chemie Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany. |

Institut für Anorganische Chemie Universität Tübingen Auf der Morgenstelle 18 72076 Tübingen Germany |

Publication type: Journal Article

Publication date: 2003-09-12

Elsevier

Tetrahedron

scimago Q3

wos Q2

SJR: 0.426

CiteScore: 4.1

Impact factor: 2.2

ISSN: 00404020, 14645416

DOI: 10.1016/j.tet.2003.08.010

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Organic Chemistry

Drug Discovery

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Abstract

Epoxidation of ethyl 3-(6-hydroxycyclohex-1-en-1-yl)propanoate ( 11 ) provided the syn epoxide 12 . By invoking chelation controlled epoxide opening the triol derivatives 13 and 14 or the spiro lactone 25 could be obtained. Elimination of HBr from the bromides 26 and 27 produced the spiro cyclohexenones 28 and 29 . Epoxidation of the double bond occurred in a diastereoselective manner to give epoxides 30 and 31 , respectively. Treatment of the epoxide 31 with LiBr/AcOH gave the bromo hydrin 38 . In a ‘merry go round’ fashion 38 was further functionalized on the cyclohexane ring by elimination, epoxidation, and epoxide opening resulting in the bromo hydrin 43 . Other cyclohexane derivatives that were produced during these studies include the cyclohexenone 19 and the cyclohexanediol 23 . In addition, enolate azidation of the spiro lactone 29 proceeded in a diastereoselective manner providing the α-azido lactone 32 .

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Eipert M., Maichle-Mössmer C., Maier M. E. Use of epoxidation and epoxide opening reactions for the synthesis of highly functionalized 1-oxaspiro[4.5]decan-2-ones and related compounds // Tetrahedron. 2003. Vol. 59. No. 40. pp. 7949-7960.

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RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.tet.2003.08.010

UR - https://doi.org/10.1016/j.tet.2003.08.010

TI - Use of epoxidation and epoxide opening reactions for the synthesis of highly functionalized 1-oxaspiro[4.5]decan-2-ones and related compounds

T2 - Tetrahedron

AU - Eipert, Martin

AU - Maichle-Mössmer, Cäcilia

AU - Maier, M. E.

PY - 2003

DA - 2003/09/12

PB - Elsevier

SP - 7949-7960

IS - 40

VL - 59

SN - 0040-4020

SN - 1464-5416

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2003_Eipert,

author = {Martin Eipert and Cäcilia Maichle-Mössmer and M. E. Maier},

title = {Use of epoxidation and epoxide opening reactions for the synthesis of highly functionalized 1-oxaspiro[4.5]decan-2-ones and related compounds},

journal = {Tetrahedron},

year = {2003},

volume = {59},

publisher = {Elsevier},

month = {sep},

url = {https://doi.org/10.1016/j.tet.2003.08.010},

number = {40},

pages = {7949--7960},

doi = {10.1016/j.tet.2003.08.010}

}

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MLA Copy

Eipert, Martin, et al. “Use of epoxidation and epoxide opening reactions for the synthesis of highly functionalized 1-oxaspiro[4.5]decan-2-ones and related compounds.” Tetrahedron, vol. 59, no. 40, Sep. 2003, pp. 7949-7960. https://doi.org/10.1016/j.tet.2003.08.010.

Publisher

Elsevier

Journal

Tetrahedron

scimago Q3

wos Q2

SJR

0.426

CiteScore

4.1

Impact factor

2.2

ISSN

00404020 (Print)

14645416 (Electronic)