cheminform abstract: new route to herbertanes via a suzuki cross-coupling reaction: synthesis of...

2002 terpenes terpenes U 0200 12 - 225 New Route to Herbertanes via a Suzuki Cross-Coupling Reaction: Synthesis of Herbertenediol. — The new approach towards herbertenediol (XVI) is based on a Suzuki cross-coupling reaction, cf. (II)→(IV), and a [2,3]-sigmatropic Still–Wittig rearrangement, cf. (VII)→(VIII), as the key steps. The complete sequence is realized with racemic alcohol (V). Application of this approach to the synthesis of herbertenediol in natural form requires enantiopure (S)-(V) and establishes a route for the enantioselective total synthesis of herbertenediol. The enantiopure form of (V) can be achieved in 92% yield and 85–88% e.e. from (IV). — (ABAD, ANTONIO; AGULLO, CONSUELO; CUNAT, ANA C.; JIMENEZ, DIEGO; PERNI, REMEDIOS H.; Tetrahedron 57 (2001) 48, 9727-9735; Dep. Quim. Org., Fac. Quim., Univ. Valencia, E-46100 Burjassot, Valencia, Spain; EN) 1

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Page 1: ChemInform Abstract: New Route to Herbertanes via a Suzuki Cross-Coupling Reaction: Synthesis of Herbertenediol

2002 terpenes

terpenesU 0200

12 - 225New Route to Herbertanes via a Suzuki Cross-Coupling Reaction:Synthesis of Herbertenediol. — The new approach towards herbertene-diol (XVI) is based on a Suzuki cross-coupling reaction, cf. (II)→(IV), anda [2,3]-sigmatropic Still–Wittig rearrangement, cf. (VII)→(VIII), as the keysteps. The complete sequence is realized with racemic alcohol (V). Applicationof this approach to the synthesis of herbertenediol in natural form requiresenantiopure (S)-(V) and establishes a route for the enantioselective totalsynthesis of herbertenediol. The enantiopure form of (V) can be achieved in92% yield and 85–88% e.e. from (IV). — (ABAD, ANTONIO; AGULLO,CONSUELO; CUNAT, ANA C.; JIMENEZ, DIEGO; PERNI, REMEDIOS H.;Tetrahedron 57 (2001) 48, 9727-9735; Dep. Quim. Org., Fac. Quim., Univ.Valencia, E-46100 Burjassot, Valencia, Spain; EN)

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