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Synlett 1993; 1993(4): 293-295
DOI: 10.1055/s-1993-22437
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Stereocontrolled Synthesis of Optically Active Plagiospirolides A and B

Nobuo Kato* , Xue Wu, Hideyuki Nishikawa, Hitoshi Takeshita
  • *Institute of Advanced Material Study, 86, Kyushu University, Kasuga-koen, Kasuga, Fukuoka 816, Japan
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Publikationsdatum:
19. März 2002 (online)

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Optically-active plagiospirolides A and B (C35-terpenoids) were synthesized by Diels-Alder reaction between independently synthesized sesquiterpenoids (diplophyllolide A and diplophyllin) and a 5-8-5-membered tricyclic diterpenic hydrocarbon prepared from a CrCl2-mediated condensate of (3S)-benzyloxy-1-iriden-7-al and (3R)-7-chloro-1-iridene. This biogenetic type total synthesis established the absolute configuration of plagiospirolides A and B.