2003
DOI: 10.1002/ange.200200556
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Jüngste Entwicklungen bei der gekreuzten Olefinmetathese

Abstract: Unter den vielen übergangsmetallvermittelten C‐C‐verknüpfenden Reaktionen ist die Olefinmetathese in den letzten Jahren durch die große Bandbreite an möglichen Umsetzungen mit käuflichen und leicht handhabbaren Katalysatoren hervorgetreten und gilt heutzutage als eine der mächtigsten Synthesemethoden in der Organischen Chemie. Die intermolekulare Variante dieser Reaktion, die Kreuzmetathese, führte trotz ihres hohen synthetischen Nutzens bis vor kurzem eher ein Schattendasein. Durch die Entwicklung neuer, bess… Show more

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Cited by 263 publications
(66 citation statements)
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“…[17] Preparation of allylic phosphate 26 (or its trans isomer) required access to allylic alcohol 25. Attempts to synthesize 25 (or its trans isomer) through catalytic cross-metathesis [18] of 23 (or its protected derivatives) with various olefin partners and catalysts resulted in less than 20 % conversion. [19] An alternative approach, involving catalytic Si-tethered ring-closing metathesis, [20] was therefore pursued.…”
Section: Methodsmentioning
confidence: 99%
“…[17] Preparation of allylic phosphate 26 (or its trans isomer) required access to allylic alcohol 25. Attempts to synthesize 25 (or its trans isomer) through catalytic cross-metathesis [18] of 23 (or its protected derivatives) with various olefin partners and catalysts resulted in less than 20 % conversion. [19] An alternative approach, involving catalytic Si-tethered ring-closing metathesis, [20] was therefore pursued.…”
Section: Methodsmentioning
confidence: 99%
“…Spiroketal 4 possesses a sterically small C19 alkyne substituent that would allow for introduction of the C20ÀC24 diene and a C11 hydroxyethyl side chain for the formation of the C1ÀC11 triene. The spiroketal precursor ketone 5 could then be accessed via a cross-metathesis [10] between enone 6 and alkene 7.…”
Section: Introductionmentioning
confidence: 99%
“…[2] We have recently reported an efficient four-step synthesis of the potent phytoestrogen 8-prenylnaringenin (2) from commercially available naringenin (1) consisting of chemoselective diacetylation of the C-7 and C-4' phenolic hydroxy groups, prenyl ether formation at C-5 À OH, domino Claisen-Cope rearrangement and deprotection (Scheme 1). [3] Here we disclose a related route that allows a completely regioselective C-6 prenylation of flavonoids belonging to different subgroups of these natural products via europiumA C H T U N G T R E N N U N G (III)-catalyzed Claisen rearrangement [4] followed by cross-metathesis (CM) [5,6] as the key events. [7] Using this approach, the flavanone 6-prenylnaringenin (3) first isolated from Humulus lupulus, [8] the isoflavone 6-prenylgenistein (wighteone, erythrinin B) (4) first isolated from Glycine wightii [9] and Erythrina variegata [10] as well as a protected derivative of the flavonol 6-prenylquercetin (gancaonin P) (5) first isolated from Glycyrrhiza uralensis [11] have been synthesized in short reaction sequences (Figure 1).…”
mentioning
confidence: 98%