title: Synthesis of bicyclic proline derivatives by the aza-Cope-Mannich reaction: formal synthesis of (±)-acetylaranotin.
abstract: Herein we suggest an approach to oxygenated bicyclic amino acids based on an aza-Cope-Mannich rearrangement. Seven distinct amino acid scaffolds analogous to the natural products were prepared on a gram scale with precise control of stereochemistry. Successful implementation of our strategy resulted in the formal synthesis of acetylaranotin.
authors: Lomonosov Moscow State University, Department of Chemistry, 1/3 Leninskie Gory, Moscow, 119991 (Russia) www.chem.msu.ru; EDASA Scientific srls., Via Stingi, 37, 66050 San Salvo (CH) (Italy) www.edasascientific.com. kurkin@direction.chem.msu.ru.
authors: Dmitry S
authors: DS
authors: Belov
authors: Nina K
authors: NK
authors: Ratmanova
authors: Ivan A
authors: IA
authors: Andreev
authors: Alexander V
authors: AV
authors: Kurkin
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D001372:Aza Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D010082:Oxepins; C006370:acetylaranotin; D011392:Proline
keywords: amino acids; medicinal chemistry; natural products; rearrangement; total synthesis