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Synthesis of the C1–C26 Northern Portion of Azaspiracid‐1: Kinetic versus Thermodynamic Control of the Formation of the Bis‐spiroketal
Author(s) -
Zhou XiaoTi,
Carter Rich G.
Publication year - 2006
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.200503733
Subject(s) - library science , chemistry , computer science
North–South divide : An efficient synthesis of the entire C1–C26 (northern) portion of azaspiracid‐1 is disclosed (see picture). Key transformations include the formation of a bis‐spiroketal, the oxidation of a sulfone at C10 to form a β,γ‐unsaturated ketone, a tandem Wadsworth–Emmons/hetero‐Michael addition to construct ring D, and the highly selective hydroxylation at C20.