ArticleNature communications2015
Total synthesis of palau'amine.
Article in Nature communications, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Efficient construction of the hexacyclic ring core of palau'amine: the pChemical science · 2021Article
- Quick construction of a C-N bond from arylsulfonyl hydrazides and CRSC advances · 2019Article
- A Nitrone Dipolar Cycloaddition Strategy toward an Enantioselective Synthesis of Massadine.Organic letters · 2018Article
- Rapid access to the core skeleton of the [3 + 2]-type dimeric pyrrole-imidazole alkaloids by triplet ketone-mediated C-H functionalization.Tetrahedron · 2018Article
- Natural products as inspiration for the development of new synthetic methods.Journal of the Chinese Chemical Society. Zhongguo hua xue hui (Taipei, Taiwan) · 2018Article
- Stereocontrolled Formation of a [4.4]Heterospiro Ring System with Unexpected Inversion of Configuration at the Spirocenter.The Journal of organic chemistry · 2017Article
- Asymmetric Synthesis of Axinellamines A and B.Angewandte Chemie (International ed. in English) · 2016Article
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Palau'amine has received a great deal of attention in the past two decades as an attractive synthetic target by virtue of its intriguing molecular architecture and significant immunosuppressive activity. Here we report the total synthesis of palau'amine characterized by the construction of an ABDE tetracyclic ring core including a trans-bicylo[3.3.0]octane skeleton at a middle stage of total synthesis. The ABDE tetracyclic ring core is constructed by a cascade reaction of a cleavage of the N-N bond, including simultaneous formation of imine, the addition of amide anion to the resulting imine (D-ring formation) and the condensation of pyrrole with methyl ester (B-ring formation) in a single step. The synthetic palau'amine is confirmed to exhibit excellent immunosuppressive activity. The present synthetic route has the potential to help elucidate a pharmacophore as well as the mechanistic details of immunosuppressive activity.
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