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Synthesis of Germacrene‐B and Its Extension to the Synthesis of (±)‐9‐Methylgermacrene‐B, the Racemate of the Male‐Produced Sex Pheromone of the Sandfly Lutzomyia longipalpis from Lapinha, Brazil
Author(s) -
Muto Shinetsu,
Nishimura Yutaka,
Mori Kenji
Publication year - 1999
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/(sici)1099-0690(199909)1999:9<2159::aid-ejoc2159>3.0.co;2-b
Subject(s) - germacrene , sandfly , sex pheromone , chemistry , stereochemistry , zoology , biology , leishmania , sesquiterpene , parasite hosting , world wide web , computer science
Both germacrene‐B ( 2 ) and 9‐methylgermacrene‐B [(±)‐ 1 ] were synthesized by employing cyclization reactions [ 8 → 9 and (±)‐ 20 → (±)‐ 21 ] as the key steps. The latter [(±)‐ 1 ] was shown to be the racemate of the male‐produced sex pheromone of the sandfly Lutzomyia longipalpis from Lapinha, Brazil.