Efficient synthesis of [2H2]-tetrahydrodicranenone B and a 3-oxa-analogue resistant against β-oxidation
作者： Ryan Lauchli , Wilhelm Boland
DOI: 10.1016/S0040-4020(02)01484-9
关键词:
摘要: Abstract A short efficient synthesis of two analogues tetrahydrodicranenone B as well a formal ( 1 ) itself has been devised. The approach is based on an addition/elimination sequence in situ prepared organocuprates to the iodocyclopentenone 9 ). procedure compatible with functionalised substituents.
mpg.de
elsevier.com
sci-hub.se 参考文章(24)
Biologically Active Natural Products : Agrochemicals CRC Press. ,(1999) , 10.1201/9781420048629
Ender Erdik, Organozinc Reagents in Organic Synthesis ,(1996)
Paul Knochel, Juan J. Almena Perea, Philip Jones, Organozinc mediated reactions Tetrahedron. ,vol. 54, pp. 8275- 8319 ,(1998) , 10.1016/S0040-4020(98)00318-4
Kunikazu Sakai, Tamotsu Fujimoto, Mitsuo Yamashita, Kiyosi Kondo, Total synthesis of (±)-dicranenones, novel cyclopentenonyl fatty acids Tetrahedron Letters. ,vol. 26, pp. 2089- 2092 ,(1985) , 10.1016/S0040-4039(00)94786-5
Barry M. Trost, Anthony B. Pinkerton, A new strategy for cyclopentenone synthesis. Organic Letters. ,vol. 2, pp. 1601- 1603 ,(2000) , 10.1021/OL005853A
G.W. Buchanan, M. Gerzain, C. Bensimon, R. Ellen, V.M. Reynolds, Stereochemistry of oxygenated 10-membered rings: X-ray crystal structure, theoretical calculations and 1H and 13C NMR studies of benzo-10-crown-3 ether in solution and in the solid phase Journal of Molecular Structure. ,vol. 404, pp. 307- 317 ,(1997) , 10.1016/S0022-2860(96)09439-2
Tetsuya Ichikawa, Misuzu Namikawa, Kaoru Yamada, Kunikazu Sakai, Kiyosi Kondo, Novel cyclopentenonyl fatty acids from mosses, and Tetrahedron Letters. ,vol. 24, pp. 3337- 3340 ,(1983) , 10.1016/S0040-4039(00)86263-2
Thomas Koch, Katja Bandemer, Wilhelm Boland, Biosynthesis of cis-jasmone: A pathway for the inactivation and the disposal of the plant stress hormone jasmonic acid to the gas phase? Helvetica Chimica Acta. ,vol. 80, pp. 838- 850 ,(1997) , 10.1002/HLCA.19970800318
Paul Knochel, Ming Chang P. Yeh, Scott C. Berk, Jason Talbert, Synthesis and reactivity toward acyl chlorides and enones of the new highly functionalized copper reagents RCu(CN)ZnI Journal of Organic Chemistry. ,vol. 53, pp. 2390- 2392 ,(1988) , 10.1021/JO00245A057
Marcel R. Kling, Christopher J. Easton, Alf Poulos, Synthesis of very long chain fatty acid methyl esters Journal of the Chemical Society, Perkin Transactions 1. pp. 1183- 1189 ,(1993) , 10.1039/P19930001183