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McClure CK, Kiessling AJ, Link JS. Oxa-di-pi-methane photochemical rearrangement of quinuclidinones. Synthesis of pyrrolizidinones. Org Lett. 2003;5(21):3811-3doi: 10.1021/ol035202p.
McClure, C. K., Kiessling, A. J., & Link, J. S. (2003). Oxa-di-pi-methane photochemical rearrangement of quinuclidinones. Synthesis of pyrrolizidinones. Organic letters, 5(21), 3811-3. https://doi.org/10.1021/ol035202p
McClure, Cynthia K, et al. "Oxa-di-pi-methane photochemical rearrangement of quinuclidinones. Synthesis of pyrrolizidinones." Organic letters vol. 5,21 (2003): 3811-3. doi: https://doi.org/10.1021/ol035202p
McClure CK, Kiessling AJ, Link JS. Oxa-di-pi-methane photochemical rearrangement of quinuclidinones. Synthesis of pyrrolizidinones. Org Lett. 2003 Oct 16;5(21):3811-3. doi: 10.1021/ol035202p. PMID: 14535716.
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Org Lett. 2003 Oct 16;5(21):3811-3. doi: 10.1021/ol035202p.

Oxa-di-pi-methane photochemical rearrangement of quinuclidinones. Synthesis of pyrrolizidinones.

Organic letters

Cynthia K McClure, Anthony J Kiessling, Jeffrey S Link

Affiliations

  1. Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, USA. [email protected]

PMID: 14535716 DOI: 10.1021/ol035202p

Abstract

[reaction: see text] The oxa-di-pi-methane (ODPM) photochemical rearrangement, a triplet-sensitized sigmatropic 1,2-acyl shift of beta,gamma-enones, was successful utilizing methyl and heptyl 1-aza-3-carboalkoxybicyclo[2.2.2]oct-2-en-5-ones (quinuclidinones) as the photoprecursors. The cyclopropane of the heptyl ester tricyclic photoproduct could be opened with lithium dimethylcuprate or via hydrogenolysis to produce the corresponding pyrrolizidinone skeletons.

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