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Synlett 2001; 2001(7): 1127-1128
DOI: 10.1055/s-2001-15149
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A New Synthesis of Methyl 3-Oxo-2-pentyl-1-cyclopentene-1-acetate

Khushrav Crawford* , Valentin Rautenstrauch, Arnold Uijttewaal
  • *Firmenich Chemical Manufacturing Center, 150 Firmenich Way, Newark, NJ 07114 USA; Fax + 1 973 344 29 99; E-mail: khushrav.crawford@firmenich.com
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Publication Date:
31 December 2001 (online)

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The 92 : 8 equilibrium mixture of (±)-trans-methyl dihydrojasmonate (1) and its cis-isomer is transformed in 63% overall yield into the title compound 4 by epoxidation of the derived enol acetate 2 with peracetic acid/Na2CO3 in toluene and heating the resulting α-acetoxy epoxide 3 in MeOH in the presence of catalytic amounts of methanesulfonic acid.

jasmonoids - enol esters - epoxidations - cyclopentenones - indirect dehydrogenations

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