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Synthesis of (-)-Picrotoxinin by Late-Stage Strong Bond Activation.
Crossley, Steven W M; Tong, Guanghu; Lambrecht, Michael J; Burdge, Hannah E; Shenvi, Ryan A.
Affiliation
  • Crossley SWM; Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
  • Tong G; Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
  • Lambrecht MJ; Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
  • Burdge HE; Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
  • Shenvi RA; Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
J Am Chem Soc ; 142(26): 11376-11381, 2020 07 01.
Article in En | MEDLINE | ID: mdl-32573211
ABSTRACT
We report a concise, stereocontrolled synthesis of the neurotoxic sesquiterpenoid (-)-picrotoxinin (1, PXN). The brevity of the route is due to regio- and stereoselective formation of the [4.3.0] bicyclic core by incorporation of a symmetrizing geminal dimethyl group at C5. Dimethylation then enables selective C-O bond formation in multiple intermediates. A series of strong bond (C-C and C-H) cleavages convert the C5 gem-dimethyl group to the C15 lactone of PXN.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Picrotoxin Language: En Journal: J Am Chem Soc Year: 2020 Document type: Article Affiliation country: Estados Unidos
Fulltext
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Picrotoxin Language: En Journal: J Am Chem Soc Year: 2020 Document type: Article Affiliation country: Estados Unidos