Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 4, Pages 1236-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja9103233
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Funding
- Ministry of Education, Culture, Sports, Science and Technology of Japan [15109001, 20002004]
- Grants-in-Aid for Scientific Research [15109001] Funding Source: KAKEN
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The total synthesis of (-)-mersicarpine was achieved in 10 steps from a known ketoester. Our synthesis features an Eschenmoser-Tanabe-type fragmentation to synthesize an alkyne unit containing a quaternary carbon center. a facile construction of the indole skeleton via a combination of a Sonogashira Coupling and a gold(Ill) catalyzed cyclization, as well as a one-pot process to arrange the cyclic imine and the hemiaminal moieties. Our synthesis unambiguously confirmed the reported structure of (-)-mersicarpine including the absolute configuration.
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