Tynacantha marginata

The asopine bug Tynacantha marginata represents a case in point of the premature designation of insect-produced compounds as pheromones. Males of this species produce a novel tricyclic sesquiterpenoid 48 from their pheromone gland , which has been designated as a putative sex pheromone [64], apparently on the basis that it is produced only by males. No assessment of the biological activity of crude extracts from the bugs, the purified compound from the bugs, or the synthetic compounds (see below) has been reported in the primary literature. 

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Isopropyl-4,6-dimethyltricyclo[4.4.05 9]dec-3-en-2-one (40) with unknown absolute configuration was isolated as a putative male pheromone of a Brazilian predatory stink bug (Tynacantha marginata), and its enantiomers were synthesized by Kuwahara as shown in Scheme 58 [88]. The triene A gave B and C by an intramolecular Diels-Alder reaction, and they could be converted to the enantiomers of 40. 

Scheme 6 Synthesis of the racemate of a novel tricyclic sequiterpenoid produced by males of the stink bug Tynacantha marginata [65]...

Scheme 7 Diels-Alder reaction of a single precursor proceeds via different transition states that produce two isomeric intermediates, each of which can be converted to one of the enantiomers of the novel Tynacantha marginata sesquiterpenoid [64]...

Kuwahara S, Hamade S, Leal WS et al (2000) Synthesis of a novel sesquiterpene isolated from the pheromone gland of a stink bug, tynacantha marginata dallas. Tetrahedron 56 8111-8117... 

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