Journal article
Investigations of an annulation-fragmentation-spirocyclisation approach to fawcettimine-type Lycopodium alkaloids
- Abstract:
- This paper reports progress in the development of a furan oxidative N-spirocyclisation approach to the fawcettimine alkaloids huperzine Q and lycopladine D. A short synthesis is described of a key intermediate cyclopentaindolizidine that subsequently fragments by N-acylation and β-elimination. The stereochemistry of 1,4-addition of cyanide to the resulting enone is discussed with supporting molecular modelling calculations. N-Deprotection is shown to be accompanied by cyclisation onto the nitrile group, resulting in a tricyclic lactam with a twisted amide functionality. Elaboration of this lactam afforded four of the five rings present in lycopladine D with just the C(8) carbon lacking.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Accepted manuscript, pdf, 851.2KB, Terms of use)
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- Publisher copy:
- 10.1016/j.tet.2019.130661
Authors
- Publisher:
- Elsevier
- Journal:
- Tetrahedron More from this journal
- Volume:
- 75
- Issue:
- 46
- Article number:
- 130661
- Publication date:
- 2019-10-04
- Acceptance date:
- 2019-09-27
- DOI:
- ISSN:
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0040-4020
- Language:
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English
- Keywords:
- Pubs id:
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pubs:1061577
- UUID:
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uuid:91abedbe-ed1b-43a5-85fd-95e40d9c28c0
- Local pid:
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pubs:1061577
- Source identifiers:
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1061577
- Deposit date:
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2019-10-11
Terms of use
- Copyright holder:
- Elsevier Ltd.
- Copyright date:
- 2019
- Rights statement:
- © 2019 Elsevier Ltd. All rights reserved.
- Notes:
-
This is the accepted manuscript version of the article. The final version is available from Elsevier at https://doi.org/10.1016/j.tet.2019.130661
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