Pheromone Synthesis, CLI. Synthesis of Chlorinated Steroids Related to the Structures Proposed for Blattellastanosides A and B, the Aggregation Pheromone of the German Cockroach, Blattella germanica L.

Medientyp: E-Artikel
Titel: Pheromone Synthesis, CLI. Synthesis of Chlorinated Steroids Related to the Structures Proposed for Blattellastanosides A and B, the Aggregation Pheromone of the German Cockroach, Blattella germanica L
Beteiligte: Mori, Kenji; Fukamatsu, Kunio; Kido, Masaru
Erschienen: Wiley, 1993
Erschienen in: Liebigs Annalen der Chemie
Sprache: Englisch
DOI: 10.1002/jlac.1993199301107
ISSN: 0170-2041
Schlagwörter: Organic Chemistry ; Physical and Theoretical Chemistry
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Beschreibung: <jats:title>Abstract</jats:title><jats:p>Remote functionalization of 5α‐stigmastan‐3β‐ol (<jats:bold>5</jats:bold>) to yield eventually 5α‐stigmast‐9(11)‐en‐3α‐ol (<jats:bold>8</jats:bold>) was employed for the syntheses of 9α‐chloro‐5α‐stigmastane‐3β,11β‐diol (<jats:bold>13</jats:bold>) and 12α‐chloro‐9α,11α‐epoxy‐5α‐stigmastan‐3β‐yl β‐<jats:sc>D</jats:sc>‐glucopyranoside (<jats:bold>3</jats:bold>). The former (<jats:bold>13</jats:bold>) was the aglycone part of the structure <jats:bold>2</jats:bold> originally proposed for blattellastanoside B, and the latter (<jats:bold>3</jats:bold>) was exactly the structure proposed for blattellastanoside A, the components of the aggregation pheromone of the German cockroach, <jats:italic>Blattella germanica</jats:italic> L. The present work disproved the structures <jats:bold>1</jats:bold>–<jats:bold>4</jats:bold> proposed for blattellastanosides A and B.</jats:p>

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