- Abstract:
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We report a 12-step catalytic enantioselective formal synthesis of malhamensilipin A (3) and diastereoisomeric analogues from (E)-2-undecenal. The convergent synthesis relied upon iterative epoxidation and phosphorus(V)-mediated deoxydichlorination reactions as well a titanium-mediated epoxide-opening to construct the C11–C16 stereohexad. The latter transformation occurred with very high levels of stereoretention regardless of the C13 configuration of the parent epoxide, implicating anchimeri...
Expand abstract - Publication status:
- Published
- Peer review status:
- Peer reviewed
- Version:
- Publisher's Version
- Files:
-
-
(pdf, 2.0mb)
-
- Publisher copy:
- 10.1039/C6SC03012B
-
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- Publisher:
- Royal Society of Chemistry Publisher's website
- Journal:
- Chemical Science Journal website
- Publication date:
- 2016
- Acceptance date:
- 2016-08-02
- DOI:
- EISSN:
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2041-6539
- ISSN:
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2041-6520
- Pubs id:
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pubs:641592
- URN:
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uri:a9a85b6f-bbc9-4347-a20f-c6181e576d9f
- UUID:
-
uuid:a9a85b6f-bbc9-4347-a20f-c6181e576d9f
- Local pid:
- pubs:641592
- Copyright holder:
- © The Royal Society of Chemistry 2016
- Copyright date:
- 2016
- Notes:
- This is the publisher's version of the article. The final version is available online from Royal Society of Chemistry at: 10.1039/C6SC03012B
Journal article
Synthesis of malhamensilipin A exploiting iterative epoxidation/chlorination: experimental and computational analysis of epoxide-derived chloronium ions
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School of Chemistry, University of Nottingham
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