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Total Synthesis of Ascospiroketal A Through a Ag I ‐Promoted Cyclization Cascade
Author(s) -
Chang Stanley,
Hur Soo,
Britton Robert
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201408905
Subject(s) - total synthesis , cascade , natural product , chemistry , stereochemistry , tricyclic , core (optical fiber) , cascade reaction , combinatorial chemistry , organic chemistry , physics , catalysis , chromatography , optics
The total synthesis of four candidate stereostructures for the marine octaketide ascospiroketal A have been achieved. These concise and highly stereocontrolled syntheses feature a unique Ag I ‐promoted cyclization cascade involving an oxetanyl ketochlorohydrin to access the entire tricyclic core of the natural product in one step. These syntheses also establish the full stereochemistry for the ascospiroketal natural products.