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A Ten‐Step Total Synthesis of Speradine C
Author(s) -
Liu Haichao,
Chen Lijun,
Yuan Kuo,
Jia Yanxing
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201902004
Subject(s) - annulation , ring (chemistry) , total synthesis , chemistry , construct (python library) , stereochemistry , salient , combinatorial chemistry , catalysis , computer science , organic chemistry , programming language , artificial intelligence
The first total synthesis of speradine C has been achieved in only ten steps from a commercially available 4‐bromoindole. Salient features of the work are the formation of four rings through three cyclizations, namely a bioinspired [3+2] annulation to form the C/D rings, an NCS‐mediated oxidation to construct the E ring, and a Ru‐catalyzed ketohydroxylation to assemble the F ring. This work highlights how strategic ring constructions can streamline the synthesis of polycyclic compounds.