✦ LIBER ✦
Natural and Unnatural A-seco Terpenes from Pulegone: Synthesis of Galbanic Acid and Marneral Revisited
✍ Scribed by Andrei Corbu; Maurizio Aquino; Manuel Perez; Zoila Gandara; Siméon Arseniyadis
- Book ID
- 102828956
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- English
- Weight
- 610 KB
- Volume
- 2009
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
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]. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)