Journal article
Total synthesis of (−)-himalensine A
- Abstract:
- The first enantioselective synthesis of (-)-himalensine A has been achieved in 22 steps. The synthesis was enabled by a novel catalytic, enantioselective prototropic shift/furan Diels-Alder (IMDAF) cascade to construct the ACD tricyclic core. A reductive radical cyclization cascade was utilized to build the B ring, and end-game manipulations featuring a molecular oxygen mediated γ-CH oxidation, a Stetter cyclization to access the pendant cyclopentenone, and a highly chemoselective lactam reduction delivered the natural product target.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
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(Accepted manuscript, pdf, 1.4MB)
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- Publisher copy:
- 10.1021/jacs.7b10956
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Authors
Funding
+ Engineering and Physical Sciences Research Council
More from this funder
Grant:
LeadershipFellowshiptoD.J.D.,
postdoctoralfellowshipstoB.D.
studentshipto
I.N.M
P.J.,
Bibliographic Details
- Publisher:
- American Chemical Society Publisher's website
- Journal:
- Journal of the American Chemical Society Journal website
- Volume:
- 139
- Issue:
- 49
- Pages:
- 17755-17758
- Publication date:
- 2017-11-09
- Acceptance date:
- 2017-11-09
- DOI:
- EISSN:
-
1520-5126
- ISSN:
-
0002-7863
- Pmid:
-
29120635
- Source identifiers:
-
746099
Item Description
- Language:
- English
- Pubs id:
-
pubs:746099
- UUID:
-
uuid:38bcc4ad-cd93-4fb3-a425-0050bc42f14d
- Local pid:
- pubs:746099
- Deposit date:
- 2018-02-09
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 American Chemical Society at: https://doi.org/10.1021/jacs.7b10956
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