Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 24, Pages 6968-6972Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01400a
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Funding
- NSFC [21971092, 21901014]
- Post-doctoral Foundation Project of Shenzhen Polytechnic [6021330005K]
- Post-doctoral Later-stage Foundation Project of Shenzhen Polytechnic [6021271005K, 6021271003K]
- Marine Medicine Innovation Platform for the Integration of Production and Education of Guangdong Provincial Education Department [2021CJPT014]
- Innovation Team of Guangdong Education Department [2022KCXTD054]
- Shenzhen Science and Technology Innovation Committee [20220815100042003, JSGG20201103153800002, GJHZ20200731095412037, JCYJ20200109141808025]
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A concise total synthesis of (+/-)-pileamartines A and B, alkaloids with an unprecedented tetracyclic skeleton, was achieved. Key steps including NHC-catalyzed tandem reaction, diastereoselective reductive allylation, and RCM were used to establish the core structure.
A concise total synthesis of (+/-)-pileamartines A and B, a pair of alkaloids sharing an unprecedented tetracyclic skeleton, was achieved in 9 and 8 linear steps, respectively. The key steps include an NHC-catalyzed tandem aza-benzoin/Michael reaction to rapidly establish the polyhydroindenopyrrole core, a diastereoselective reductive allylation of pyrrolidone, and an RCM to construct the piperidine ring.
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