Bs. Lindsay et al., EFFICIENT AND CONVENIENT PYRIDINE RING-E FORMATION OF THE CYTOTOXIC MARINE ALKALOID ASCIDIDEMIN AND RELATED ANALOGS, Synthetic communications, 27(15), 1997, pp. 2587-2592
Conversion of tetracyclic quinone 1 to the cytotoxic pentacyclic alkal
oid ascididemin (2) in 80% yield is achieved by reaction with paraform
aldehyde and ammonium chloride in refluxing acetic acid. High yielding
annelations are also observed for the related analogues N-8 deaza asc
ididemin (3) and kuanoniamine A (4).