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Natural and Unnatural A‐ seco Terpenes from Pulegone: Synthesis of Galbanic Acid and Marneral Revisited
Author(s) -
Corbu Andrei,
Aquino Maurizio,
Perez Manuel,
Gandara Zoila,
Arseniyadis Siméon
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901021
Subject(s) - pulegone , terpene , chemistry , terpenoid , stereochemistry , yield (engineering) , organic chemistry , food science , materials science , essential oil , metallurgy
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)