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(-)-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...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/acs.orglett.7b00434

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Institution:
University of Oxford
Oxford college:
Magdalen College
Role:
Author
More by this author
Institution:
University of Oxford
Oxford college:
St Catherine's College
Role:
Author
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:
1523-7052
ISSN:
1523-7060
Language:
English
Keywords:
Pubs id:
pubs:686930
UUID:
uuid:8d1d3e58-ca91-4a78-b749-084f3f459560
Local pid:
pubs:686930
Source identifiers:
686930
Deposit date:
2017-06-02

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