An Approach to Serrulatane Diterpenes via e ndo-Selective Conjugate Nucleophilic Addition to Arene-Cr(CO)3 Complexes

An Approach to Serrulatane Diterpenes via e ndo-Selective Conjugate Nucleophilic Addition to Arene-Cr(CO)3 Complexes

Starting from a nonracemic planar-chiral arene tricarbonyl chromium complex, the serrulatane diterpenoid (+)-20-methoxy-serrulat-14-en-7,8-diol was synthesized in a highly stereoselective fashion. The key step of the synthesis is an endo-selective conjugate nucleophilic addition of lithio-methylphen...

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Veröffentlicht in:Organic letters 2002-10, Vol.4 (22), p.3915-3918
Hauptverfasser: Dehmel, Florian, Lex, Johann, Schmalz, Hans-Günther
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Lex, Johann
Schmalz, Hans-Günther
description Starting from a nonracemic planar-chiral arene tricarbonyl chromium complex, the serrulatane diterpenoid (+)-20-methoxy-serrulat-14-en-7,8-diol was synthesized in a highly stereoselective fashion. The key step of the synthesis is an endo-selective conjugate nucleophilic addition of lithio-methylphenyl sulfone to a 1-ethylidene-tetralin-Cr(CO)3 derivative. By employing different substrates and nucleophiles it was shown that the surprising and rather general endo selectivity must result from a unique complex induced proximity effect under participation of the Cr(CO)3 moiety.
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Lett</addtitle><date>2002-10-31</date><risdate>2002</risdate><volume>4</volume><issue>22</issue><spage>3915</spage><epage>3918</epage><pages>3915-3918</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Starting from a nonracemic planar-chiral arene tricarbonyl chromium complex, the serrulatane diterpenoid (+)-20-methoxy-serrulat-14-en-7,8-diol was synthesized in a highly stereoselective fashion. The key step of the synthesis is an endo-selective conjugate nucleophilic addition of lithio-methylphenyl sulfone to a 1-ethylidene-tetralin-Cr(CO)3 derivative. By employing different substrates and nucleophiles it was shown that the surprising and rather general endo selectivity must result from a unique complex induced proximity effect under participation of the Cr(CO)3 moiety.</abstract><pub>American Chemical Society</pub><doi>10.1021/ol026827a</doi><tpages>4</tpages></addata></record>
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