Synthesis of (.+-.)-endo- and (.+-.)-exo-brevicomin via ene reaction of the Pummerer rearrangement product derived from 4-chlorophenyl methyl sulfoxide.

Ishibashi, Hiroyuki; Uehara, Chiaki; Komatsu, Hajime; Ikeda, Masazumi

doi:10.1248/cpb.35.2750

Cited by 10 publications

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“…The Pummerer reaction involving primary product 108 afforded numerous biologically active compounds, for example, the sex pheromone of red cotton moth (109) with the ratio of the (E )-and (Z )-isomers identical to that observed in the natural substance, 75 the pheromone of some tortricids 110 76 and bicyclic exo-brevicomin 111, which is the aggregation pheromone of fir moth (in a mixture with 11% of the endo epimer). 77 Trideca-(4E,7Z )-4,7-dien-1-ol acetate (112), which is the potato moth pheromone, was synthesised 78 starting from phosphorus-substituted sulfide 113. The latter was derived from (methylsulfinyl)phosphonate by the Pummerer reaction followed by the reaction with 5-heptyl acetate.…”

Section: Syntheses Based On Intermolecular Reactions Of Sulfenium Cat...mentioning

confidence: 99%

Rearrangements of sulfoxides and sulfones in the total synthesis of natural compounds

Prilezhaeva¹

2001

Russ. Chem. Rev.

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AbsbaCL An alomcdly ordered PdCu&o.p hydride was spthesizcd at 600 K and a hydxogcn p m s m of 3 GPa Irs Netd lanice had B primitive temgonal cell fomcd from the initial K c cell of thc disordcred PdCu alloy due to ordcrbg of the Pd and Cu atoms into allemve la)cn perpendicul;lr to the tetragonal c-ais. Rietveld refinemcat of Ihe neumn diffraction pallem of P d C u b 9 m a u r e d ai 80 K showcd thc H ~o m s to occupy octahedral interstitials within thc Pd layers. The inclastic neumu scanering sNdy at 35 K revealed a broad hydrogen o p i d peak with pcculivlties at energy m s f c n of 79 and 95 meV and of I13 meV uhich wcre zcribed to the H vibrations in the P d H planes and dong thc CU-H chains perpendiculv to the planer, respectively. The paantid for hydmgen *OM in the PdCK+9 ordered phase was thus noticeably diffcrenc even in the Pd-H plane, from that in the h o u n hydrides of pdhdium and palladium alloys. The value of approximly 116 meV was predicted forthc l o d H vibntions in dilute Cu-H solid solutions. E G 1991 Physica B 174 25741 Sov. Phys.-Solid State 33 87-90 Calcu&fions: User Manual (IFF KFA, Jiilich) Jiil-Spa-366 Rev. B 36 8798-801 A I, Bashkin IO, Sinicyn V V and Ponyatovskii E G 1989 Physlca C 162-164 1369-70 Belushkin A V 1993 Phys. Solid Srate 35 99-103

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