Preparation of (1R,8S)- and (1S,8R)-9-azabicyclo[6.2.0]dec-4-en-10-one: potential starting compounds for the synthesis of anatoxin-a |
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| Institution: | 1. From the Division for Heart Disease and Stroke Prevention, National Center for Chronic Disease Prevention and Health Promotion, Atlanta, GA (CIM, MEC, and ALV); the Division of Health and Nutrition Examination Surveys, National Center for Health Statistics, Hyattsville, MD (C-YW), the Centers for Disease Control and Prevention; National Heart, Lung, and Blood Institute, NIH, Bethesda, MD (CML); the Beltsville Human Nutrition Research Center, Agricultural Research Service, USDA, Beltsville, MD (AJM and DGR); and the Department of Statistics, Iowa State University, Ames, IA (ALC).;1. Univ. Estadual Paulista—UNESP, Departamento de Fisiologia, Instituto de Biociências, CEP 18618-970, Botucatu, SP, Brazil;2. Univ. Estadual Paulista—UNESP, Faculdade de Ciências Farmacêuticas, CEP 14800-902, Araraquara, SP, Brazil;3. Universidade São Francisco, Faculdade de Ciências Médicas, Unidade Integrada de Farmacologia e Gastroenterologia, CEP 12916-900, Bragança Paulista, SP, Brazil;4. Univ. Estadual Paulista—UNESP, Campus Experimental do Litoral Paulista, CEP 11330-900, São Vicente, SP, Brazil;1. School of Material Science and Engineering, Wuhan Institute of Technology, Wuhan 430074, China;2. Institute for Materials Research, Tohoku University, 2-1-1 Katahira, Sendai 980-8577, Japan |
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| Abstract: | 9-Azabicyclo6.2.0]dec-4-en-10-one (±)-2, obtained from cyclooctadiene by addition of chlorosulfonyl isocyanate, was N-hydroxymethylated to (±)-3 and then resolved by lipase-catalysed asymmetric acylation of the primary OH group at the (S)-stereogenic centre. High enantioselectivity (E=94) was observed when lipase PS and vinyl butyrate were used in di-iso-propyl ether at ?15°C, resulting in the enantiomerically enriched ester 3a and alcohol 3b (e.e. ≥92%). Treatment of 3a and 3b with NH4OH/MeOH afforded the corresponding β-lactams (1R,8S)-2a and (1S,8R)-2b (e.e. ≥93%), potential starting compounds in anatoxin-a synthesis. The ring opening of lactams (±)-2, (±)-7, 3a and 3b, followed by reduction, resulted in racemic 4–6 and 8 and enantiomeric 4a, 4b, 5a and 5b eight-membered cyclic β-amino acid derivatives. |
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