Total synthesis of α-bisabolol-3-one and deodarone

Bromomalonates as synthetic reagents. Transfer alkylations

“…The resulting solution was stirred 15 min at -20 OC and cooled to -78 OC. 3-6.5 (m, C-2,4,5.7,8 vinyl H); uv (ethanol) 226 nm, t 21 900; 249 nm, t 5790; mass spectrum m/e (re1 intensity) 396 (5). The resulting orange solution was stirred 35 min at -78 OC and then poured via a stainless steel tube into a -78 OC solution of 185 pI (2.97 mmol) of methyl iodide in I O ml of dry tetrahydrofuran.…”

“…The resulting orange solution was stirred 35 min at -78 OC and then poured via a stainless steel tube into a -78 OC solution of 185 pI (2.97 mmol) of methyl iodide in I O ml of dry tetrahydrofuran. 365 (19), 351 ( 5 ) , 350 (12). The resulting red solution was poured into ether-water and extracted twice with ether.…”

Deodarone Isomers in Cedrus atlantica Essential Oils and Tar Oils

“…As early as 1973, Shankaranarayanan et al [1] obtained a mixture of deodarone isomers via bis-epoxidation of -atlantone. Later, Gopichand and Chakravarti [3] synthesized a mixture of deodarone isomers starting from isoprene and methyl vinyl ketone. A few years later, the compound has been synthesized from limonene via a reaction with -unsaturated nitrile oxide [4].…”

Modificação do produto natural (-)-∝- Bisabolol

“…Encontra-se na literatura varias sínteses do bisabolol e derivados, as principais são (APSIMON, 1983;CAHIEZ, 1988;SWANSON, 1979;GOPICHAND;CHAKRAVARTI, 1974;VIG, 1976;KERGOMARD;VESCHAMBRE, 1977;LIM;CHEON, 2003;MANJARREZ;GUZMAN, 1966;NEMOTO et al, 1993), entretanto a literatura consultada é muito pobre sobre trabalhos de modificações do (-)-α-bisabolol, provavelmente devido às dificuldades de trabalhar com este tipo de estrutura química.…”

“…6.9). O Deodarone ( é um produto natural extraído da madeira Cedrus deodara (GOPICHAND, 1974), é proveniente do rearranjo da cetona alílica da dupla acíclica do bisabolol. Dados FTIR (KBr), ν (cm -1 ) : 3363,2965,2925,1770,1450,1382,1301,1286,1261,1246,1193,1141,1112,1086,1043,1008,951,936,903,801,653.…”