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Natural and Unnatural A-seco Terpenes from Pulegone: Synthesis of Galbanic Acid and Marneral Revisited

  作者 CORBU ANDREI; AQUINO MAURIZIO; PEREZ MANUEL; GANDARA ZOILA; ARSENIYADIS SIMEON  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2009年-36;  页码  6386-6392  
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[摘要]We describe herein an improved chiral-pool strategy for assembling the core structure 3 (both antipodes) of various A-seco terpenoids that have allowed us to prepare natural galbanic acid [(-)-1] from (S)+)-pulegone [(+2]. Furthermore, we were able to increase both the yield and step efficiency of the synthesis of marneral [(+)-7] as well as to access higher homologues of ent-galbanic acid [(+)-4], ent-secodrial [(+)-5], and bis-epi-secochiliotrin (6) from (R)-(+)-pulegone [(+)-2]. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

 
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