Solvolytic hydroperoxide rearrangements V. A stereoselective synthesis of trans-fused butyrolactones. |
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| Institution: | 1. Departamento de Farmacología, Universidad de Valencia, Valencia, Spain;2. CNRS UMR 6014, C.O.B.R.A. & FR 3038, Université de Rouen, INSA de Rouen, 76131 Mont-Saint-Aignan Cedex, France;3. BioCIS, Université Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France;4. Instituto de Investigación Sanitaria - INCLIVA, Hospital Clínico Universitario de Valencia, Valencia 46010, Spain;5. Institut Pasteur de Lille, Univ. Lille - EGID, CHU Lille, Inserm U1011, F-59000 Lille, France;6. Institut de Recherches Servier, 92150 Suresnes, France;1. Instituto Nacional de Ciência e Tecnologia em Tuberculose, Centro de Pesquisas em Biologia Molecular e Funcional, Pontifícia Universidade Católica do Rio Grande do Sul, 90616-900, Porto Alegre, Rio Grande do Sul, Brazil;2. Programa de Pós-Graduação em Medicina e Ciências da Saúde, Pontifícia Universidade Católica do Rio Grande do Sul, 90616-900, Porto Alegre, Rio Grande do Sul, Brazil;3. Programa de Pós-Graduação em Biologia Celular e Molecular, Pontifícia Universidade Católica do Rio Grande do Sul, 90616-900, Porto Alegre, Rio Grande do Sul, Brazil;4. Global Health and Tropical Medicine, GHTM, Instituto de Higiene e Medicina Tropical, IHMT, Universidade NOVA de Lisboa, UNL, Lisbon, Portugal;1. Astbury Centre for Structural Molecular Biology, University of Leeds, Leeds LS2 9JT, UK;2. School of Chemistry, University of Leeds, Leeds LS2 9JT, UK;3. H3D Drug Discovery and Development Center, University of Cape Town, Private Bag, Rondebosch 7700, South Africa;4. Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa;5. Institute of Infectious Disease and Molecular Medicine, University of Cape Town, Rondebosch 7701, South Africa;6. South African Medical Research Council, Drug Discovery and Development Research Unit, University of Cape Town, Rondebosch 7701, South Africa;1. Department of Chemistry, Washington State University, Pullman, WA 99164, USA;2. Cardiovascular Center of Excellence, Louisiana State University Health Science Center, New Orleans, LA 70112, USA;3. Department of Chemistry, Southern Illinois University Edwardsville, Edwardsville, IL 62026, USA |
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| Abstract: | Stereoselective rearrangement of cis-5-(4-methoxybenzyl)-spiro5,2]-octan-4-ol cis-1 in acidified THF-90% H2O2 affords 9-oxabicyclo6.2.1]nonyl hydroperoxides 7 and 8 which are converted to medium-ring, keto-butyrolactones 2 and 3. |
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