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Synthesis of Both the Enantiomers Invictolide, a Pheromone Component of the Red Imported Fire Ant by Kenji Mori; Yutaka Nakazono is a Chemistry article available to read on EtoBox.

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Both the -tiomers of invictolide 13,5~methyld-(l'laethylbutyl)tetrahydro-2H-pyran-2-l were synthesized in 17 steps from ~hopargyl alcohol. Invictolide 1 (=C) is one of the three lactones (A, B and C) isolated from the red imported fire ant (Solenopsis invicta Buren) as the queen recognition pheromone."\* The lactone A is an achiral compound, and was synthesized by Rocca et al' -2 As to dihydroactinidiolide B, we recently reported a synthesis of the both of its enantiomers. 3 Invictolide 1 possesses four chiral centers. Its relative stereochemistry was shown to be 3R\*,5R\*,6g\*,l'R\* as depicted in 1 by Rocca's synthesis of (\*)-1.' Since then, three additional syntheses of (i)-1 were announced as preliminary communications. 4-6 Ziegler's success in synthesizing (3&5S,6&,1'S)-(+)-invictolide 1' made Its bioassay possible.7 The fact that (+)-1' was biologically inactive while (iI-1 was active suggested the absolute configuration of natural invictolide to be 3&5&6S,l'R as depicted in 1. Yerein we report in detail our own approach to the synthesis of invictolide enantiomers, which culminated in the preparation of both (-)-1 and (+)-1' as crystals. Our synthesis of invictolide was line

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Author

Kenji Mori; Yutaka Nakazono

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1986

Language

EN

Field

Chemistry (Physical Sciences)