Synthetic studies towards oxygenated and unsaturated furanocembranoid macrocycles. Precursors to plumarellide, rameswaralide and mandapamates

作者: Gerald Pattenden , Johan M. Winne

DOI: 10.1016/J.TETLET.2010.07.102

关键词:

摘要: A new approach to the synthesis of oxygenated furanocembranoids, exemplified by danielid 3, is described. The features an intermolecular Knoevenagel-type condensation together with intramolecular aldolisation elaborate furan and lactone rings, respectively, in initial target compound 14. Efforts isomerise C13–C14 double bond, or introduce alkene bond at C11–C12 14, leading structures 3 8, are

参考文章(19)
Paul A. Roethle, Dirk Trauner, The chemistry of marine furanocembranoids, pseudopteranes, gersolanes, and related natural products Natural Product Reports. ,vol. 25, pp. 298- 317 ,(2008) , 10.1039/B705660P
Leo A. Paquette, Peter C. Astles, Total synthesis of furanocembranolides. 3. A concise convergent route to acerosolide The Journal of Organic Chemistry. ,vol. 58, pp. 165- 169 ,(1993) , 10.1021/JO00053A031
Manuel Cases, Felix Gonzalez-Lopez de Turiso, Maria S. Hadjisoteriou, Gerald Pattenden, Synthetic studies towards furanocembrane diterpenes. A total synthesis of bis-deoxylophotoxin Organic and Biomolecular Chemistry. ,vol. 3, pp. 2786- 2804 ,(2005) , 10.1039/B504545B
Gerald Pattenden, Johan M. Winne, An intramolecular [4+3]-cycloaddition approach to rameswaralide inspired by biosynthesis speculation Tetrahedron Letters. ,vol. 50, pp. 7310- 7313 ,(2009) , 10.1016/J.TETLET.2009.10.046
Brandon Doroh, Gary A. Sulikowski, Progress toward the total synthesis of Bielschowskysin: a stereoselective [2+2] photocycloaddition. Organic Letters. ,vol. 8, pp. 903- 906 ,(2006) , 10.1021/OL0530225
Jean-François Lavallée, Claude Spino, Réjean Ruel, Keith T. Hogan, Pierre Deslongchamps, Stereoselective synthesis of cis-decalins via Diels–Alder and double Michael addition of substituted Nazarov reagents Canadian Journal of Chemistry. ,vol. 70, pp. 1406- 1426 ,(1992) , 10.1139/V92-179
Miguel A. González, Subhash Ghosh, Fatima Rivas, Derek Fischer, Emmanuel A. Theodorakis, Synthesis of (+)- and (-)-isocarvone Tetrahedron Letters. ,vol. 45, pp. 5039- 5041 ,(2004) , 10.1016/J.TETLET.2004.04.181
Kenji Mori, Kunio Fukamatsu, Pheromone Synthesis, CXXXVII. A New Synthesis of (+)-Grandisol Liebigs Annalen der Chemie. ,vol. 1992, pp. 489- 493 ,(1992) , 10.1002/JLAC.199219920187
Daniela Grote, Hans-Martin Dahse, Karlheinz Seifert, Furanocembranoids from the Soft Corals Sinularia asterolobata and Litophyton arboreum Chemistry & Biodiversity. ,vol. 5, pp. 2449- 2456 ,(2008) , 10.1002/CBDV.200890210