An intramolecular [4+3]-cycloaddition approach to rameswaralide inspired by biosynthesis speculation

作者: Gerald Pattenden , Johan M. Winne

DOI: 10.1016/J.TETLET.2009.10.046

关键词:

摘要: Abstract A concise synthesis of the polycycle 27 , which incorporates 5,5,7-tricyclic ring core rameswaralide 1 using a biogenetically inspired acid-catalysed [4+3]-cycloaddition approach starting from furanobutenolide 26 is described, namely, 26→28 / 29→27 . Under thermal conditions, same gives alternative polycyclic compound 35 resulting [4+2]-cycloaddition involving furan as dienophile.

参考文章(18)
Ernest. Wenkert, Peter D. R. Moeller, Serge R. Piettre, Five-membered aromatic heterocycles as dienophiles in Diels-Alder reactions. Furan, pyrrole, and indole Journal of the American Chemical Society. ,vol. 110, pp. 7188- 7194 ,(1988) , 10.1021/JA00229A039
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
Stewart N. Abramson, Jacqueline A. Trischman, Dianne M. Tapiolas, Edward E. Harold, William Fenical, Palmer Taylor, Structure/activity and molecular modeling studies of the lophotoxin family of irreversible nicotinic receptor antagonists. Journal of Medicinal Chemistry. ,vol. 34, pp. 1798- 1804 ,(1991) , 10.1021/JM00110A007
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
Ammanamanchi S.R. Anjaneyulu, Kadali S. Sagar, Mukku J.R.V. Venugopal, Terpenoid and steroid constituents of the Indian ocean soft coral Sinularia maxima Tetrahedron. ,vol. 51, pp. 10997- 11010 ,(1995) , 10.1016/0040-4020(95)00655-R
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
Seiki Saito, Takashi Hasegawa, Masami Inaba, Ryosuke Nishida, Toshikazu Fujii, Seiya Nomizu, Toshio Moriwake, COMBINATION OF BORANE-DIMETHYL SULFIDE COMPLEX WITH CATALYTIC SODIUM TETRAHYDROBORATE AS A SELECTIVE REDUCING AGENT FOR α-HYDROXY ESTERS. VERSATILE CHIRAL BUILDING BLOCK FROM (S)-(−)-MALIC ACID Chemistry Letters. ,vol. 13, pp. 1389- 1392 ,(1984) , 10.1246/CL.1984.1389
Y. Venkateswarlu, K. V. Sridevi, M. Rama Rao, New furanocembranoid diterpenes from the soft coral sinularia maxima Journal of Natural Products. ,vol. 62, pp. 756- 758 ,(1999) , 10.1021/NP9804076
Y. Venkateswarlu, M.A. Farooq Biabani, M. Venkata Rami Reddy, T. Prabhakar Rao, A.C. Kunwar, D. John Faulkner, Mandapamate, a diterpenoid from the soft coral sinularia dissecta☆ Tetrahedron Letters. ,vol. 35, pp. 2249- 2252 ,(1994) , 10.1016/S0040-4039(00)76811-0