A concise ring-expansion route to the compact core of platensimycin

Nicholas A. McGrath; Emily S. Bartlett; Satapanawat Sittihan; Jon T. Njardarson

doi:10.1002/anie.200903347

A concise ring-expansion route to the compact core of platensimycin

Nicholas A. McGrath
, Emily S. Bartlett
, Satapanawat Sittihan
, Jon T. Njardarson

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

73 Scopus citations

Abstract

Oxatropanes from oxiranes: An expedient assembly of the compact platensimycin core is described. The synthetic approach relies on a Suzuki cross-coupling, a late-stage dearomatization reaction, and a copper-catalyzed vinyl oxirane ring expansion for accessing the oxatropane moiety of the natural product.

Original language	English (US)
Pages (from-to)	8543-8546
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	45
DOIs	https://doi.org/10.1002/anie.200903347
State	Published - Oct 26 2009
Externally published	Yes

Keywords

Copper
Natural products
Oxiranes
Platensimycin
Total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200903347

Cite this

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abstract = "Oxatropanes from oxiranes: An expedient assembly of the compact platensimycin core is described. The synthetic approach relies on a Suzuki cross-coupling, a late-stage dearomatization reaction, and a copper-catalyzed vinyl oxirane ring expansion for accessing the oxatropane moiety of the natural product.",

keywords = "Copper, Natural products, Oxiranes, Platensimycin, Total synthesis",

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AU - McGrath, Nicholas A.

AU - Bartlett, Emily S.

AU - Sittihan, Satapanawat

AU - Njardarson, Jon T.

PY - 2009/10/26

Y1 - 2009/10/26

N2 - Oxatropanes from oxiranes: An expedient assembly of the compact platensimycin core is described. The synthetic approach relies on a Suzuki cross-coupling, a late-stage dearomatization reaction, and a copper-catalyzed vinyl oxirane ring expansion for accessing the oxatropane moiety of the natural product.

AB - Oxatropanes from oxiranes: An expedient assembly of the compact platensimycin core is described. The synthetic approach relies on a Suzuki cross-coupling, a late-stage dearomatization reaction, and a copper-catalyzed vinyl oxirane ring expansion for accessing the oxatropane moiety of the natural product.

KW - Copper

KW - Natural products

KW - Oxiranes

KW - Platensimycin

KW - Total synthesis

UR - https://www.scopus.com/pages/publications/70350303174

UR - https://www.scopus.com/pages/publications/70350303174#tab=citedBy

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M3 - Article

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SN - 1433-7851

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

A concise ring-expansion route to the compact core of platensimycin

Abstract

Keywords

ASJC Scopus subject areas

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