Controlled beta-hydride elimination during tetrahydropyran formation with Pd(II); diastereoselective formation of the tetrahydropyran ring of tetronomycin

M. F. Semmelhack; Chung Ryeol Kim; Walter Dobler; Michael Meier

doi:10.1016/S0040-4039(01)80544-X

Controlled beta-hydride elimination during tetrahydropyran formation with Pd(II); diastereoselective formation of the tetrahydropyran ring of tetronomycin

M. F. Semmelhack, Chung Ryeol Kim, Walter Dobler, Michael Meier

Chemistry

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

64 Scopus citations

Abstract

The use of DMSO solvent allows control of beta-hydride elimination following alkoxy-palladation of alkenes, producing a side chain trans alkene unit on 2,6-disubstituted tetrahydropyrans. The method is applied towards the synthesis of tetronomycin.

Original language	English (US)
Pages (from-to)	4925-4928
Number of pages	4
Journal	Tetrahedron Letters
Volume	30
Issue number	37
DOIs	https://doi.org/10.1016/S0040-4039(01)80544-X
State	Published - 1989

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)80544-X

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title = "Controlled beta-hydride elimination during tetrahydropyran formation with Pd(II); diastereoselective formation of the tetrahydropyran ring of tetronomycin",

abstract = "The use of DMSO solvent allows control of beta-hydride elimination following alkoxy-palladation of alkenes, producing a side chain trans alkene unit on 2,6-disubstituted tetrahydropyrans. The method is applied towards the synthesis of tetronomycin.",

author = "Semmelhack, {M. F.} and Kim, {Chung Ryeol} and Walter Dobler and Michael Meier",

note = "Funding Information: Acknowledgement. We are pleased to acknowledge support from the National Institutes of Health (research grant GM 31352) and postdoctoral fellowships (DAAD) to WD and MM.",

year = "1989",

doi = "10.1016/S0040-4039(01)80544-X",

language = "English (US)",

volume = "30",

pages = "4925--4928",

journal = "Tetrahedron Letters",

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T1 - Controlled beta-hydride elimination during tetrahydropyran formation with Pd(II); diastereoselective formation of the tetrahydropyran ring of tetronomycin

AU - Semmelhack, M. F.

AU - Kim, Chung Ryeol

AU - Dobler, Walter

AU - Meier, Michael

N1 - Funding Information: Acknowledgement. We are pleased to acknowledge support from the National Institutes of Health (research grant GM 31352) and postdoctoral fellowships (DAAD) to WD and MM.

PY - 1989

Y1 - 1989

N2 - The use of DMSO solvent allows control of beta-hydride elimination following alkoxy-palladation of alkenes, producing a side chain trans alkene unit on 2,6-disubstituted tetrahydropyrans. The method is applied towards the synthesis of tetronomycin.

AB - The use of DMSO solvent allows control of beta-hydride elimination following alkoxy-palladation of alkenes, producing a side chain trans alkene unit on 2,6-disubstituted tetrahydropyrans. The method is applied towards the synthesis of tetronomycin.

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U2 - 10.1016/S0040-4039(01)80544-X

DO - 10.1016/S0040-4039(01)80544-X

M3 - Article

AN - SCOPUS:0024349946

SN - 0040-4039

VL - 30

SP - 4925

EP - 4928

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Controlled beta-hydride elimination during tetrahydropyran formation with Pd(II); diastereoselective formation of the tetrahydropyran ring of tetronomycin

Abstract

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