S. Marchais et al., Synthesis of the marine carbinolamine (+/-) longamide control of N-1 and C-3 bromopyrrole nucleophilicity, TETRAHEDR L, 40(30), 1999, pp. 5519-5522
A short synthesis of (i+/-) longamide 1 using a probable biomimetic cyclisa
tion of 12 is described. The separation of its enantiomeric forms and their
racemisation are examined. The ring-chain tautomerism involving a potentia
l nucleophilicity of N-1/C3 of bromopyrrole compounds has been examined. Th
e behaviour of 7 in protic mild or in vigorous acidic conditions provides a
n entry to regioselective synthesis of marine polycycle alkaloids such as 2
, 3, and 4. A biogenetic pathway is proposed for polycyclic 2-aminoimidazol
opyrrole marine metabolites. (C) 1999 Elsevier Science Ltd. All rights rese
rved.