Evaluation of alkene isomerization as a trigger for enediyne activation

M. F. Semmelhack; Richmond Sarpong; Jeffrey Bergman; Douglas M. Ho

doi:10.1016/S0040-4039(01)02139-6

Evaluation of alkene isomerization as a trigger for enediyne activation

M. F. Semmelhack, Richmond Sarpong, Jeffrey Bergman, Douglas M. Ho

Chemistry

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

8 Scopus citations

Abstract

The concept of non-conjugated-to-conjugated double bond isomerization as a triggering mechanism for a calicheamicin model was tested. A bicyclo[7.3.1] enediyne framework was prepared with a bridgehead double bond and an acetonyl side chain. Base-promoted exchange failed to produce the conjugated isomer. Computational analysis suggested that additional conjugating groups would favor the isomerization, but experiment proved that not to be correct.

Original language	English (US)
Pages (from-to)	541-544
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	4
DOIs	https://doi.org/10.1016/S0040-4039(01)02139-6
State	Published - Jan 21 2002

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Alkene isomerization
Enediynes
Enol-keto isomerization

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10.1016/S0040-4039(01)02139-6

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abstract = "The concept of non-conjugated-to-conjugated double bond isomerization as a triggering mechanism for a calicheamicin model was tested. A bicyclo[7.3.1] enediyne framework was prepared with a bridgehead double bond and an acetonyl side chain. Base-promoted exchange failed to produce the conjugated isomer. Computational analysis suggested that additional conjugating groups would favor the isomerization, but experiment proved that not to be correct.",

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AU - Semmelhack, M. F.

AU - Sarpong, Richmond

AU - Bergman, Jeffrey

AU - Ho, Douglas M.

PY - 2002/1/21

Y1 - 2002/1/21

N2 - The concept of non-conjugated-to-conjugated double bond isomerization as a triggering mechanism for a calicheamicin model was tested. A bicyclo[7.3.1] enediyne framework was prepared with a bridgehead double bond and an acetonyl side chain. Base-promoted exchange failed to produce the conjugated isomer. Computational analysis suggested that additional conjugating groups would favor the isomerization, but experiment proved that not to be correct.

AB - The concept of non-conjugated-to-conjugated double bond isomerization as a triggering mechanism for a calicheamicin model was tested. A bicyclo[7.3.1] enediyne framework was prepared with a bridgehead double bond and an acetonyl side chain. Base-promoted exchange failed to produce the conjugated isomer. Computational analysis suggested that additional conjugating groups would favor the isomerization, but experiment proved that not to be correct.

KW - Alkene isomerization

KW - Enediynes

KW - Enol-keto isomerization

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 4

ER -

Evaluation of alkene isomerization as a trigger for enediyne activation

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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