Synthesis of the marine carbinolamine (+/-) longamide control of N-1 and C-3 bromopyrrole nucleophilicity

Authors
Marchais, S Al Mourabit, A Ahond, A Poupat, C Potier, P
Citation
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
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
30
Year of publication
1999
Pages
5519 - 5522
Database
ISI
SICI code
0040-4039(19990723)40:30<5519:SOTMC(>2.0.ZU;2-F
Abstract
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.