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Total Synthesis and Configurational Assignment of Ascospiroketal A
Author(s) -
Chang Stanley,
Hur Soo,
Britton Robert
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502754
Subject(s) - computer science
The total synthesis of the marine fungus‐derived natural product ascospiroketal is described. This concise synthesis relies on a unique Ag I ‐promoted tandem cascade cyclization that provides direct access to the correctly configured tricyclic core of the natural product from a linear precursor. The synthesis of candidate stereostructures of ascospiroketal A allowed for the confident assignment of both the relative and absolute stereochemistry of this unusual octaketide.