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Synthesis of malhamensilipin A exploiting iterative epoxidation/chlorination: experimental and computational analysis of epoxide-derived chloronium ions

Abstract:

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...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Publisher's Version

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Publisher copy:
10.1039/C6SC03012B

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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Denton, RM More by this author
School of Chemistry, University of Nottingham More from this funder
Publisher:
Royal Society of Chemistry Publisher's website
Journal:
Chemical Science Journal website
Publication date:
2016
Acceptance date:
2016-08-02
DOI:
EISSN:
2041-6539
ISSN:
2041-6520
Pubs id:
pubs:641592
URN:
uri:a9a85b6f-bbc9-4347-a20f-c6181e576d9f
UUID:
uuid:a9a85b6f-bbc9-4347-a20f-c6181e576d9f
Local pid:
pubs:641592

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