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Total Synthesis of Coibacin D by Using Enantioselective Allylation and Metathesis Reactions
Author(s) -
Kolská Kristýna,
Ghavre Mukund,
Pour Milan,
Hybelbauerová Simona,
Kotora Martin
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600022
Subject(s) - enantioselective synthesis , chemistry , total synthesis , carbene , metathesis , stereochemistry , absolute configuration , catalysis , salt metathesis reaction , metabolite , combinatorial chemistry , organic chemistry , biochemistry , polymer , polymerization
The first asymmetric total synthesis of coibacin D, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp., was achieved in six steps starting from simple hept‐6‐en‐1‐ol. The synthetic strategy was based on a chiral Brønsted acid catalyzed enantioselective allylboration and a Ru‐carbene complex catalyzed sequential ring‐closing and cross‐metathesis strategy. The recorded spectroscopic data and the sign of the optical rotation of the synthesized coibacin D were in agreement with the published data for the isolated compound, which confirmed the proposed structure and absolute configuration.