Synthesis of a cis-perhydroazulene derivative related to grayanotoxin

✍ Scribed by Toshikatsu Okuno; Tekeshi Matsumoto

• Publisher: Elsevier Science
• Year: 1969
• Tongue: French
• Weight: 208 KB
• Volume: 10
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)88619-6

✦ Synopsis

dihydroq-traue4ecal.b derivatiw oftsps&(the mirror -1s shorn) and in fact a atipler perene my&en&h been obtained from a ZJ-cholestan-q-o1 devivatlw 2) . On the other hand, solvolysis of ld-me~yloq+Q,6~ -cia-decalin der%vat.iw of atemid type suchasc_lssupposedto~eld, as~inthe~~,ac~~~~~edthcon-foraationAss one of the possible prodnctd). Intbispaper~ahouldliketoreport formation of the latter type cls-parh+oaculene frcm 13. q_ -. C '\ The ld&Gqoxyketone i', m.p. SO-1410, (&D+220(c-00.82, CEC13) was obtained from 4,4- dimethylcholest-1,5-dien-j-one by treatment with alkaline hydrogen peroxide. Sodinmborohydride reduction of the ketone&gave a mixture of tw epimere, which wan sepnrated by chromatography on silica gel to g1w2 anditi the ratio of 3 tc 2;2 I.PO 109-llOe, @I, -38.6'(c=lJtg, CEC13),4_, m.p. l58-159'. (d),+6'(c=O.86, CHCf). Theepoqalcohol~rasthen converted into the corresponding tetrahydropyrsnyl ether 5, m.p. 144-145'. CHC13), snd LiAlE14 reduction of this compound gaw &lcorpoundA cd),-4%=wJ5* m.p. 148-149".