Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 49, Pages 17755-17758Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b10956
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Funding
- Syngenta
- EPSRC Centre for Doctoral Training in Synthesis for Biology and Medicine [EP/L015838/1]
- AstraZeneca
- Diamond Light Source
- Defence Science and Technology Laboratory
- Evotec
- GlaxoSmithKline
- Janssen
- Novartis
- Pfizer
- Takeda
- UCB
- Vertex
- European Union's Horizon research and innovation programme under Marie Sklodowska-Curie grant [752491, 676108]
- EPSRC
- EPSRC [EP/G007802/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [1515061, EP/G007802/1] Funding Source: researchfish
- Marie Curie Actions (MSCA) [752491] Funding Source: Marie Curie Actions (MSCA)
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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 gamma-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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