5.6- Dioxabicyclo octene

Similarly, bromination of a dioxabicyclo-octene 48 or 49 gave good yield of 50 in 98% purity. Neither the origin of the high stereoselectivity nor the stabilization of the requisite e co-radical 51 over the other radicals was explained. ... 

Novotny, M., Schwende, F.J., Wiesler, D., Jorgenson, J.W. and Carmack, M. (1984) Identification of a testosterone-dependent unique volatile constituent of male mouse urine 7-exo-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]-3-octene. Experientia 40, 217-219. 

B) Western balsam bark beetle, Dryocoetes confusus formation of endo-brevicomin [(1 F ,5S,7S)-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1 ]octane] from ( )-6-nonen-2-one (Vanderwel et a/., 1992a) (C) Spruce beetle, Dendroctonus rufipennis formation of frontalin [(1S, 5fl)-(-)-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane] from 6-methyl-6-hepten-2-one (Perez ef a/., 1996 Francke etai, 1995 Francke and Schulz, 1999) (D) European elm bark beetle, Scolytus multistriatus hypothetical formation of oc-multistriatin [(1 S,2F ,4S,5F )-(-)-2,4-dimethyl-5-ethyl-6,8-dioxabicyclo[3.2.1]octane] from 4,6-dimethyl-7-octen-3-one (Francke and Schulz, 1999) and E The colored... 

A, M. Trozzolo (Bell Telephone Laboratories) The benzil-sensitized photo-oxygenation of 1,3-cyclohexadiene in pentane-ether solution, with 3500-A. light gave the endoperoxide, 5,6-dioxabicyclo [2,2,2] 2-octene. Benzophenone was also used as the sensitizer in this study. 

Novotny, M., F.J. Schwende, D. Wiesler, J.W. Jorgenson, and M. Carmack Identification of a Testosterone-Dependent Unique Volatile Constituent of Male Mouse Urine 7-exo-Ethyl-5-Methyl-6,8-Dioxabicyclo-[3.2.1.]-3-Octene. Experientia 40, 217-219(1984). 

Fig. 12.1 Aggregation pheromones of (a) Ips paraconfusus, three male-produced synergistic components - (+ )2-methyl-6-methylene-2,7-octadien-4-ol (ipsdienol) (-)2-methyl-6-methylene-7-octen-4-ol (ipsenol) and cw-verbenol. (b) Dendroctonus brevicomisj three attractive components, cxo-7-ethyl-5-methyl-6,8-dioxabicyclo-[3.2.1] octane (cxo-brevicomin) from the female l,5-dimethyl-6,8-dioxabicyclo-[3.2.1] octane (frontalin) from the male and myrcene released from the host tree. Verbenone and trans-verbenol, released after a male locates the female, interrupts response to the attractant blend.

Chemoenzymatic asymmetric total synthesis of (S)-7,7-dimethyl -6,8-dioxabicyclo [3.2.1]octane, which is a volatile contributor to the aroma of beer, was also accomplished using lyophilized cells of R. ruber DSM 44540 in an enantioconvergent enz5miatic step. Inversion at the stereogenic center of (R)-2-methyl-7-octene-2,3-diol,... 

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