Journal article
Synthesis of (E)-4-methylhexa-3,5-dien-1-ol and its Diels-Alder reaction with thioester dienophiles: a short enantioselective synthesis of bicyclic lactones
- Abstract:
- The preparation of (E)-4-methylhexa-3,5-dien-1-ol has been achieved in a single step from 3-methylpenta-1,4-diene via deprotonation with BuLi, alkylation with paraformaldehyde, and metal counterion exchange in situ to promote oxy-anion accelerated [1,3]-sigmatropic shift. This alcohol is shown to undergo intermolecular Diels-Alder reaction with 3-isopropyl acrylate thioesters; the so-formed exclusive endo-adduct may then be closed to the bicyclic lactone, the product of formal intramolecular Diels-Alder reaction (a much more difficult process). Use of chiral thioesters results in an enantioselective synthesis of this bicyclic lactone, an intermediate with application to eunicellane (cladiellane) diterpene synthesis.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
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(Preview, Accepted manuscript, pdf, 1.6MB, Terms of use)
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- Publisher copy:
- 10.1002/ejoc.201700900
Authors
- Publisher:
- Wiley
- Journal:
- European Journal of Organic Chemistry More from this journal
- Volume:
- 2017
- Issue:
- 33
- Pages:
- 4916–4921
- Publication date:
- 2017-07-14
- Acceptance date:
- 2017-07-14
- DOI:
- EISSN:
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1099-0690
- ISSN:
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1434-193X
- Keywords:
- Pubs id:
-
pubs:709058
- UUID:
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uuid:18a4954f-83b5-43dc-91e0-b63500fa4bf4
- Local pid:
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pubs:709058
- Source identifiers:
-
709058
- Deposit date:
-
2017-07-24
Terms of use
- Copyright holder:
- © 2017 WILEY-VCH Verlag GmbH & Co KGaA, Weinheim
- Copyright date:
- 2017
- Notes:
- This is the author accepted manuscript following peer review version of the article. The final version is available online from Wiley at: 10.1002/ejoc.201700900
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