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Enantioselective Synthesis of the Lomaiviticin Aglycon Full Carbon Skeleton Reveals Remarkable Remote Substituent Effects during the Dimerization Event
Author(s) -
Lee Hong Geun,
Ahn Jae Young,
Lee Amy S.,
Shair Matthew D.
Publication year - 2010
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.201002157
Subject(s) - substituent , natural product , enantioselective synthesis , annulation , event (particle physics) , chemistry , stereochemistry , carbon skeleton , stereoselectivity , combinatorial chemistry , computer science , organic chemistry , catalysis , physics , quantum mechanics
A full carbon skeleton of the natural product lomaiviticin has been synthesized. The approach features anionic annulation reactions to deliver A and B rings of the natural product, and stereoselective oxidative enolate coupling to form the central C2C2′ σ bond. In the course of the investigation, a remarkable substituent effect at C11 position was observed.