Open AccessA Formal Total Synthesis of the Marine Diterpenoid Diisocyanoadociane
Author(s) -
Kelly A. Fairweather,
Lewis N. Mander
Publication year - 2006
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol061228f
Subject(s) - curtius rearrangement , chemistry , terpenoid , intramolecular force , total synthesis , formal synthesis , pyrene , stereochemistry , organic chemistry
[Structure: see text] A formal total synthesis of diisocyanoadociane, a marine diterpenoid with potent antimalarial properties, has been completed. The synthesis begins with a phenanthrenoid precursor that is transformed into a pyrene-derived intermediate by means of an intramolecular Michael reaction. Nitrogen functionality is introduced via a double Curtius reaction.
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