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- W2051230714 abstract "Abstract Both the (1 S ,2 R ) and (1 R ,2 S ) isomers of 2,6,6‐trimethylbicyclo[5.4.0]undec‐7‐en‐9‐one ( 1 ) were synthesized by starting from ( S )‐ and ( R )‐citronellal ( 5 ), respectively. The stereochemistry of (1 R ,2 S )‐(−)‐ 1 was established by an X‐ray analysis; it exhibits a CD spectrum similar to that of cholest‐4‐en‐3‐one, in agreement with its absolute configuration. The ketones (1 S ,2 R )‐ and (1 R ,2 S )‐ 1 were converted into the enantiomers of three other himachalene hydrocarbons, 2,2,6‐trimethyl‐10‐methylenebicyclo[5.4.0]undec‐1(11)‐ene ( 2 ), 1,1,5,8‐tetramethyl‐1,2,3,4,5,6,5a‐heptahydrobenzo[1,2‐ a ][7]annulene ( 3 ), and 1,1,5,8‐tetramethyl‐1,2,3,4,5‐pentahydrobenzo[ a ][7]annulene ( ar ‐himachalene, 4 ). The stereochemistry of these himachalene‐type sesquiterpenes isolated from flea beetles such as Aphthona flava and Phyllotreta cruciferae as their male‐pheromone components was revised to (1 S ,2 R )‐ 1 , (6 R ,7 S )‐ 2 , (5 R ,5a S )‐ 3 , and ( R )‐ 4 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)" @default.
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- W2051230714 date "2004-04-13" @default.
- W2051230714 modified "2023-09-27" @default.
- W2051230714 title "Synthesis and Stereochemistry of the Four Himachalene‐Type Sesquiterpenes Isolated from the Flea Beetle (<i>Aphthona flava</i>) as Pheromone Candidates" @default.
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- W2051230714 doi "https://doi.org/10.1002/ejoc.200300812" @default.
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