Verbenyl acetate

Both a- and P-pinenes are popular starting materials for the synthesis of other monoterpene chiral synthons such as carvone, terpineol, and camphor (vide infra). Reactions leading to other monoterpenes are briefly summarized in Figure 5.1. Treatment of a-pinene with lead tetraacetate followed by rearrangement gives trans-verbenyl acetate (7), which is hydrolyzed to yield trans-verbenol (8) 8 Subsequent oxidation of 8 gives verbenone (9), which can be reduced to give cw-verbenol... 

Bomyl acetate (77) and verbenyl acetate mimic the activity of the American cockroach sex pheromone (Bowers, 1985). 

Nishino, C., Takayanagi, H. and Manabe, S. (1982). Comparison of sex pheromonal activity on the American cockroach between acetates and propionates of verbenyl type alcohols. Agricultural and Biological Chemistry 46 2781-2785. 

The cyclic ether (219) was converted into (220), which underwent rearrangement to (221) in a manner analogous to the celebrated norcaradiene ring-walk stereochemical analysis of the rearrangement indicated predominant inversion of configuration for both the photolytic and thermal processes and so symmetry considerations of the Woodward-Hoffman type may not be relevant to these (or at least the thermal) processes.559 Esters of pinocarveol were converted into myrtenyl compounds by CuOAc.560 cis- and rrans-Verbenyl and verbanyl acetates,561 562 related compounds563 and 2-methylverbanone564 have been synthesized for evaluation as attractants for cockroaches. 

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