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Synlett 1993; 1993(3): 191-192
DOI: 10.1055/s-1993-22396
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Natural Products Synthesis by Retro Diels-Alder Reactions IV:1 Total Synthesis of (±)-Invictolide and (±)-6-Epiinvictolide

Zhi-Yu Liu* , Ling He, Hu Zheng
  • *Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, People's Republic of China
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Publication Date:
19 March 2002 (online)

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Efficient total syntheses of (±)-invictolide 8 and its 6-epimer 9 are described. Starting from enone 4, tandem conjugate addition-enolate trapping with aldehydes, followed by another 1,4-addition and retro Diels-Alder ŕeaction, afforded key intermediates 12a and 12b which were converted into precursors 15a and 15b through hydrogenation and Baeyer-Villiger oxidation.