A Formal Total Synthesis of the Marine Diterpenoid Diisocyanoadociane

A Formal Total Synthesis of the Marine Diterpenoid Diisocyanoadociane

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 functiona...

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Veröffentlicht in:Organic letters 2006-07, Vol.8 (15), p.3395-3398
Hauptverfasser: Fairweather, Kelly A, Mander, Lewis N
Format: Artikel
Sprache:eng
Schlagworte:
Animals
Antimalarials - chemical synthesis
Antimalarials - pharmacology
Diterpenes - chemical synthesis
Diterpenes - pharmacology
Marine Biology
Molecular Structure
Nitriles - chemical synthesis
Nitriles - pharmacology
Porifera - chemistry
Pyrenes - chemical synthesis
Pyrenes - pharmacology
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol061228f