Journal article
(-)-Pseudodistomin E: First asymmetric synthesis and absolute configuration assignment
- Abstract:
- (-)-Pseudodistomin E has been prepared for the first time, allowing its structure and absolute configuration to be confirmed. The established conjugate addition of lithium (S)-N-allyl-N-(α-methyl-p-methoxybenzyl)amide to methyl (E,E)-hepta-2,5-dienoate generated the C(2)-stereocenter, and iodolactonisation of a derivative generated the remaining two stereogenic centers. Ensuing iodide displacement was achieved using a tethering strategy, to introduce the nitrogen atom to C(5). Decarboxylative coupling of a carboxylic acid with a dialkylzinc reagent completed construction of the tridecadienyl chain.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
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(Preview, Accepted manuscript, pdf, 142.0KB, Terms of use)
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- Publisher copy:
- 10.1021/acs.orglett.7b00434
Authors
- Publisher:
- American Chemical Society
- Journal:
- Organic Letters More from this journal
- Volume:
- 19
- Issue:
- 7
- Pages:
- 1638-1641
- Publication date:
- 2017-03-17
- Acceptance date:
- 2017-03-13
- DOI:
- EISSN:
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1523-7052
- ISSN:
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1523-7060
- Language:
-
English
- Keywords:
- Pubs id:
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pubs:686930
- UUID:
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uuid:8d1d3e58-ca91-4a78-b749-084f3f459560
- Local pid:
-
pubs:686930
- Source identifiers:
-
686930
- Deposit date:
-
2017-06-02
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2017
- Notes:
- Copyright © 2017 American Chemical Society. This is the accepted manuscript version of the article. The final version is available online from the American Chemical Society at: https://doi.org/10.1021/acs.orglett.7b00434
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