Enantioselective Synthesis of the Lomaiviticin Aglycon Full Carbon Skeleton Reveals Remarkable Remote Substituent Effects during the Dimerization Event | Zendy

Lee Hong Geun | Zendy; Ahn Jae Young | Zendy; Lee Amy S. | Zendy; Shair Matthew D. | Zendy

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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.

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