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“…Many important skeletons or potentially useful compounds in drug discovery have been synthesized by these methods [5] . Especially, intermolecular or intramolecular cycloaddition reactions using vinylallenes, such as [4+1], [1a–f] [4+2], [1g–m] [4+4], [1n] [4+4+1], [1o] and [3+2]/[2+3] [1p] cycloadditions, developed, respectively by Siegel et al., Murakami et al., and Lee and co‐workers, have become powerful methods to synthesize various ring compounds (Scheme 1 a). It is interesting to note that all these ring formation reactions (except one in Scheme 1 b, see below) using vinylallenes cannot be used to synthesize seven‐membered rings.…”
Section: Methodsmentioning
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“…Many important skeletons or potentially useful compounds in drug discovery have been synthesized by these methods [5] . Especially, intermolecular or intramolecular cycloaddition reactions using vinylallenes, such as [4+1], [1a–f] [4+2], [1g–m] [4+4], [1n] [4+4+1], [1o] and [3+2]/[2+3] [1p] cycloadditions, developed, respectively by Siegel et al., Murakami et al., and Lee and co‐workers, have become powerful methods to synthesize various ring compounds (Scheme 1 a). It is interesting to note that all these ring formation reactions (except one in Scheme 1 b, see below) using vinylallenes cannot be used to synthesize seven‐membered rings.…”
Section: Methodsmentioning
“…[5] More recently the wound-healing properties of these root extracts, which had drifted into folklore, were confirmed experimentally by Papageorgiou, and the active components identified as 1, 2, and closely related derivatives. [6] These natural products exhibit many other interesting biological effects including antibacterial, [7] antifungal, [8] anti-inflammatory, [9] antitu- (1) and shikonin (2). mor, [10] analgesic, [9a,11] antipyretic, [12] and immunostimulatory [13] activities.…”
Section: Methodsmentioning
“…Owing to the relatively low electron density of the allenyl group in 1 c, the cationic catalyst with phosphane ligands may not be sufficiently cationic to cleave bond (b) in 1 c, so that 2 c is preferentially formed for steric reasons (entry 7). The low regioselectivity of the reactions catalyzed by [RhCl(PPh 3 ) 3 ] (entries 3, 6, and 9) can be explained by assuming the formation of a trigonal-bipyramidal intermediate [8] in which the interaction of both bonds (a) and (b) with rhodium leads to a mixture of 2 and 3.…”
mentioning
“…Ene/yne-ene-propargyl esters were used as the substrates and we reasoned that under Rh catalysis,1 ,3acyloxy migration [10] of ene/yne-ene-propargyl esters could occur to give Rh and ene/yne-ene-allene complex I. [11] Then oxidative cyclization took place to give five-membered rhodacycle II, [12] [13] [4+ +2] (from intermediate III) [11] and [2+ +2+ +1] (from intermediate IV), [9] which had been previous realized separately by similar intermediates,c ould occur in this situation and completely make our efforts to [4+ +2+ +1] cycloaddition fruitless. We hypothesized that transformation from I to II is an intramolecular process and could be favored over possible competing intermolecular [4+ +1] reaction pathway of I with CO.I ntermediate III has as trong Rh-C bond with the original allene moiety and would not be easy to undergo reductive elimination to give [4 + 2] cycloadduct.…”
mentioning