B Damascenone Belongs To A Family Of Fragrant Natural Products Called Rose Ketones That Have Been Used In The Perfume In 1 (78.15 KiB) Viewed 62 times
B-Damascenone belongs to a family of fragrant natural products called rose ketones that have been used in the perfume industry. In one synthesis of B-damascenone, the reaction of compound 1 with one equivalent of MCPBA afforded two constitutionally isomeric epoxides (compounds 2 and 3), which were then converted into diol 4 upon subsequent treatment with aqueous acid. (Synthetic Communications 2007, 37, 1077-1090) Identify the structures of epoxides 2 and 3, and propose a mechanism that converts each of them into compound 4 in the presence of H30+. (Note: It is reasonable to presume that a protonated epoxide can open by itself, without the involvement of a nucleophile, if doing so will give a resonance-stabilized allylic carbocation intermediate.) OCH OH OCH H30+ MCBPA (one equiv.) 2 + 3 1 OH B-Damascenone
Add any missing curved arrows to complete the mechanism for the conversion of compound 2 into compound 4. راع ا,H OMe ,CH تارH OMe ية: ع )H QMe CH, CH CH, CH را C" CH + « - - - *-*-* OMe ب: ,HGH Me H.C CH, OH OMe ات: H, G H CH CH, CH, CH CH CH, OM Edit Drawing
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