Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 21, Pages 13818-13836Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01930
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Funding
- National Natural Science Foundation of China [91856202]
- National Key R&D Program of China [2019YFA09005000]
- Key Research Program of Frontier Sciences [QYZDYSSWSLH026]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
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In this report, a unified biomimetic approach to all known macrocyclic lankacidins is presented. By taking advantage of the thermolysis of N,O-acetal to generate the requisite N-acyl-1-azahexatriene species, we eventually realized the biomimetic Mannich macrocyclization, from which all of the macrocyclic lankacidins can be conquered by orchestrated desilylation. The reassignments of the reported structures of isolankacidinol (7 to 10) and the discovery of a recently isolated lankacyclinol found to be in fact 2,18-bis-epi-lankacyclinol (72) unraveled the previously underappreciated chemical diversity exhibited by the enzymatic macrocyclization. In addition, the facile elimination/decarboxylation/protonation process for the depletion of Cl under basic conditions resembling a physiological environment may implicate more undiscovered natural products with variable C2/C18 stereochemistries (i.e., 62, 73, and 75). The notable aspect provided by a biomimetic strategy is significantly reducing the step count compared with the two previous entries to macrocyclic lankacidins.
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