Abstract
AbstractThe synthesis of the (±)‐form of the marine sesquiterpene (–)‐Δ9(12)‐capnellene (1) by double application of the a‐alkynone cyclization is described. Starting with 2, 2, 5‐trim ethylcyclopentanone (2), the elaboration of the tricyclo [6.3.0.02,6]undecane C‐skeleton of 1 proceeded through the a‐alkynone 3, which was cyclized thermally to the bicyclo [3.3.0]octenone 4. For the anellation of the third five‐membered ring, 4 was transformed into the a‐alkynone 5 and the latter cyclized thermally to a mixture of the angular triquinenone 6 and the linear triquinenone 7. The last steps in the synthesis of (±)‐Δ9(12)‐capnellene (1) were then accomplished from 7 by known methods.
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