AI Article Synopsis
- The solvolysis of a specific compound in a water-saturated MeNO(2) environment yielded a 55% result of a migration product that was further processed into a methyl hexanoate with a 25% yield over five steps.
- Following the creation of this hexanoate, treatment with MeLi produced a tertiary alcohol, which was then dehydrated to synthesize an organic compound known as (R)-(-)-curcumene.
- Additionally, introducing a hydroxyl group on the aromatic ring involved a series of three transformations, ultimately leading to another tertiary alcohol that was dehydrated to produce (R)-(-)-xanthorrizol.
Article Abstract
Solvolysis reaction of methyl (4S,5S)-4-(4'-methoxyphenyl)-5-tosyloxy-2(E)-hexenoate 5 in water-saturated MeNO(2) gave the 1,2-migration product, (4S,5S)-5-hydroxy-4-(4'-methoxyphenyl)-2-(E)-hexenoate 6 (55% yield), which was converted to methyl (R)-(4'-methylphenyl)hexanoate 11 in 25% overall yield (5 steps). Treatment of (R)-11 with MeLi gave tertiary alcohol congener 12, which was subjected to dehydration to afford (R)-(-)-curcumene 1. An introduction of hydroxyl group at meta-position of the aromatic ring in (R)-11 was achieved based on consecutive treatment [1) selective iodination, 2) conversion of aryl iodide to aryl boronate, 3) conversion of aryl boronate to phenol]. Thus obtained phenol (R)-16 was treated with MeLi to give tertiary alcohol congener 17, which was subjected to dehydration to afford (R)-(-)-xanthorrizol 2.
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| http://dx.doi.org/10.1248/cpb.55.1361 | DOI Listing |
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