By L.A. Paquette
ISBN-10: 0387118284
ISBN-13: 9780387118284
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Y'. "l 2. H202,0H- H"'''~ /'''~ 4. ~, L~,NH5 H. . . . l < ~ C02Me ~ 0 1. LIN( SIMes)2 2. t N HCI 5, KOH 4. HsO+ 5. Ac20, pY ~ - - ~ 0 OH Scheme LII1 I. OH2, Ac20, py H 5. PCC C02Me b 200"C O 0 ;02H 606 The starting material in Burke's phenomenologically different approach to quadrone was a spiro[4,5]decadienone which is readily available from 2-methyldimedone isobutyl ether (Scheme LIV)357) Oxidative cleavage of the trisubstituted double bond in 606 set the stage for controlled intramolecular Michael addition (1t--,,12) 12), Once aldol cyclization to give 607 had been accomplished, the remaining major obstacle was installation of the lactone ring.
3 558 Experimental studies delineating an extensive number of chemical transformations of laurenene (532) 3t2,336), including the crystal structure analysis of a bromo derivative 337),have been published. 88 A Cedranoids VII Synthesis of Diquinane Natural Products A Cedranoids Although cedranoid sesquiterpenes have earlier been synthesized, a renewed interest in alternative methods for elaborating these frameworks has arisen. The stereospecific approach to ~-cedrene and ~-patchoulene skeletons designed by Deslongchamps and summarized in Scheme XLIII is a case in point 338).
H OH . H ""OH . SeO2 . OH _- ~. ,,,.! HI 0 i1 . H H 684 688 . H 687 OH H Scheme L X X I 685 3 Coriolin Coriolin (689), a metabolite of the Basidiomycete Coriolus consors, has attracted widespread interest because of its unusual anti-tumor activity and highly functionalized triquinane structure. Accordingly, a number of syntheses of 689 have appeared on the scene. , begins with epoxide 690, whose preparation had been earlier realized in connection with their work on hirsutine (see Scheme LXIII).
Recent Synthetic Developments in Polyquinane Chemistry by L.A. Paquette
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