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Complexity generation by chemical synthesis: a five-step synthesis of (-)-chaetominine from L-tryptophan and its
Chu-Pei Xu1, Shi-Peng Luo, Ai-E Wang
1Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China.
Abstract:
We demonstrated, for the first time, that on the basis of chemistry principles, the hexacyclic peptidyl alkaloid (−)-chaetominine (1) can be synthesized in a straightforward manner from L-Trp. The approach features the efficient generation of molecular complexity via a tandem C3/C14 syn-selective epoxidation (dr = 3:2)–annulative ring-opening reaction and a regioselective epimerization at C14. The successful production of (−)-chaetominine (1) from L-Trp could be helpful for revealing how the configuration of L-tryptophan becomes inverted in the biosynthetic pathway of (−)-chaetominine (1).
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