Total Synthesis of (−)-Himalensine A

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 b...

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Published inJournal of the American Chemical Society Vol. 139; no. 49; pp. 17755 - 17758
Main Authors Shi, Heyao, Michaelides, Iacovos N, Darses, Benjamin, Jakubec, Pavol, Nguyen, Quynh Nhu N, Paton, Robert S, Dixon, Darren J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 13.12.2017
Amer Chemical Soc
Subjects
Chemical Sciences
Chemistry
Chemistry, Multidisciplinary
Organic chemistry
Physical Sciences
Science & Technology
CHEMISTRY
CALYCIPHYLLINE
ISOMERIZATION
ALKALOIDS
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Summary: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.
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ObjectType-Article-1
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content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b10956