A formal total synthesis of the marine diterpenoid diisocyanoadociane.
[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.
Fairweather
Kelly A
KA
Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.
Mander
Lewis N
LN
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000494:pharmacology; D004224:Diterpenes / Q000138:chemical synthesis* / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry; D011721:Pyrenes / Q000138:chemical synthesis* / Q000494:pharmacology
D000962:Antimalarials; D004224:Diterpenes; D009570:Nitriles; D011721:Pyrenes; C424431:diisocyanoadociane