Formale Totalsynthese von (±)‐Isocomen durch Anwendung der α‐Alkinon‐Cyclisierung

DOI Web Site Web Site 被引用文献2件

抄録

<jats:p><jats:bold>Formal Total Synthesis of (±)‐Isocomen by Application of the α‐Alkinon Cyclization</jats:bold></jats:p><jats:p>A total synthesis of the racemic form of the sesquiterpene isocomene (<jats:bold>A</jats:bold>) was accomplished by application of the cyclopentenone anellation <jats:bold>B→D</jats:bold> <jats:italic>(Scheme 1)</jats:italic> which includes the α‐alkynone cyclization <jats:bold>C→D</jats:bold>, a gas‐phase flow thermolytic process. Starting with the known product <jats:bold>2</jats:bold> <jats:italic>(Scheme 3)</jats:italic> of the anellation <jats:bold>B→D</jats:bold>, the elaboration of ring <jats:bold>C</jats:bold> of <jats:bold>A</jats:bold> proceeded in 9 steps to the α‐alkynone <jats:bold>16</jats:bold> <jats:italic>(Scheme 5)</jats:italic> which was cyclized at 540° selectively to give the angularly fused triquinane <jats:bold>4</jats:bold> (77%). A two‐step procedure then led to <jats:bold>5</jats:bold> <jats:italic>(Scheme 6)</jats:italic>, a last but one intermediate in a known total synthesis of (±)‐<jats:bold>A</jats:bold>. The conversion of <jats:bold>16</jats:bold> to <jats:bold>4</jats:bold> also demonstrated the compatibility of an acetoxy function with the anellation sequence <jats:bold>B→D</jats:bold>.</jats:p>

収録刊行物

被引用文献 (2)*注記

もっと見る

キーワード

詳細情報 詳細情報について

問題の指摘

ページトップへ