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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
Version:
Accepted Manuscript

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Publisher copy:
10.1021/jacs.7b10956

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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Role:
Author
ORCID:
0000-0002-2431-9732
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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Role:
Author
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Grant:
Leadership Fellowship to D.J.D., postdoctoral fellowships to B.D. and P.J., and studentship to I.N.M.
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Grant:
stu-dentship to I.N.M
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Grant:
Marie Skłodowska-Curie grant agreement No. 676108
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
Pubs id:
pubs:746099
URN:
uri:38bcc4ad-cd93-4fb3-a425-0050bc42f14d
UUID:
uuid:38bcc4ad-cd93-4fb3-a425-0050bc42f14d
Local pid:
pubs:746099
Paper number:
49
Language:
English

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