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A Two‐Step Chemoenzymatic Synthesis of the Natural Pheromone (+)‐Sitophilure Utilizing Isolated, NADPH‐Dependent Ketoreductases
Author(s) -
Kalaitzakis Dimitris,
Rozzell J. David,
Kambourakis Spiros,
Smonou Ioulia
Publication year - 2006
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.200500991
Subject(s) - sitophilus , chemistry , pheromone , rice weevil , yield (engineering) , total synthesis , stereochemistry , organic chemistry , botany , biology , materials science , metallurgy
Isolated, NADPH‐dependent ketoreductases were used for the synthesis of the aggregation pheromone of the pests rice weevil ( Sitophilus oryzae L.) and maize weevil ( Sitophilus zeamais M.). This is the easiest and most straight forward synthesis of pheromone (+)‐Sitophilure in two steps and an overall yield of 81 %, starting from commercially available 3,5‐heptanedione. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)