A concise enantiocontrolled total synthesis of (−)-α-bisabolol and (+)-4-epi-α-bisabolol

Nemoto, Hideo; Shiraki, Motohiro; Nagamochi, Masatoshi; Fukumoto, Keiichiro

doi:10.1016/s0040-4039(00)74051-2

Cited by 29 publications

(12 citation statements)

References 25 publications

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“…The reaction showed lower efficiency in the absence of A1, affording 4a in 37% yield ( Table 1, entry 2). Increasing the loading of A1 to 10 mol% and 20 mol% did not further improve the yield of 4a ( [6][7][8]. No desired product was detected in the absence of nickel catalyst or sacrificial reductant zinc (Table 1, entry 9).…”

Section: Resultsmentioning

confidence: 96%

“…ultiple substituted alkenes are pivotal subunits which are commonly occurring in natural products [1][2][3] , bioactive molecules [4][5][6][7] , and material sciences 8 , and serve as useful precursors for other functional groups and chiral centers [9][10][11][12] . In addition, alkenes exhibit orthogonal reactivity with respect to polar functional groups, providing an opportunity for the late-stage derivatization of complex molecules.…”

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confidence: 99%

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Ni-catalyzed regio- and stereo-defined intermolecular cross-electrophile dialkylation of alkynes without directing group

2021

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The development of straightforward synthesis of regio- and stereodefined alkenes with multiple aliphatic substituents under mild conditions is an unmet challenge owing to competitive β-hydride elimination and selectivity issues. Herein, we report the nickel-catalyzed intermolecular cross-dialkylation of alkynes devoid of directing or activating groups to afford multiple aliphatic substituted alkenes in a syn-selective fashion at room temperature. The combination of two-electron oxidative cyclometallation and single-electron cross-electrophile coupling of nickel enables the syn-cross-dialkylation of alkynes at room temperature. This reductive protocol enables the sequential installation of two different alkyl substituents onto alkynes in a regio- and stereo-selective manner, circumventing the tedious preformation of sensitive organometallic reagents. The synthetic utility of this protocol is demonstrated by efficient synthesis of multi-substituted unfunctionalized alkenes and diverse transformations of the product.

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Section: Resultsmentioning

confidence: 96%

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confidence: 99%

Ni-catalyzed regio- and stereo-defined intermolecular cross-electrophile dialkylation of alkynes without directing group

2021

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“…Alkyl- and aryl-substituted cyclopropylidene alcohols delivered cyclobutanones such as 448 – 450 in good yields and high enantioselectivities. The same group applied this strategy to the enantioselective total synthesis of various biologically active compounds. − …”

Section: Alkylidenecyclopropanesmentioning

confidence: 99%

Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes

2020

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This review describes the development of enantioselective methods for the ring opening of cyclopropanes. Both approaches based on the reaction of nonchiral cyclopropanes and (dynamic) kinetic resolutions and asymmetric transformations of chiral substrates are presented. The review is organized according to substrate classes, starting by the more mature field of donor−acceptor cyclopropanes. Emerging methods for enantioselective ring opening of acceptor-or donor-only cyclopropanes are then presented. The last part of the review describes the ring opening of more reactive three-membered rings substituted with unsaturations with a particular focus on vinylcyclopropanes, alkylidenecyclopropanes, and vinylidenecyclopropanes. In the last two decades, the field has grown from a proof of concept stage to a broad range of methods for accessing enantioenriched building blocks, and further extensive developments can be expected in the future.

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“…The data on the synthesis of ␣-bisabolol available in the literature are very scarce [11][12][13][14][15][16][17][18][19][20][21][22][23]. All the works (mostly patents) report the use of nerolidol or farnesol as starting materials [11][12][13][14][15][16] except for the articles describing total syntheses [17][18][19][20][21][22][23]. In most of the procedures, the synthesis of ␣-bisabolol from farnesol or nerolidol is performed in the presence of large amounts of strong acids, usually mineral acids, and gives the product in 30-50% yields.…”

Section: Introductionmentioning

confidence: 99%

Heteropoly acid catalyzed cyclization of nerolidol and farnesol: Synthesis of α-bisabolol

Meireles

Costa

Rocha

et al. 2015

Applied Catalysis A: General

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A concise enantiocontrolled total synthesis of (−)-α-bisabolol and (+)-4-epi-α-bisabolol

Cited by 29 publications

References 25 publications

Ni-catalyzed regio- and stereo-defined intermolecular cross-electrophile dialkylation of alkynes without directing group

Ni-catalyzed regio- and stereo-defined intermolecular cross-electrophile dialkylation of alkynes without directing group

Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes

Heteropoly acid catalyzed cyclization of nerolidol and farnesol: Synthesis of α-bisabolol

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