Direct synthesis of pyran-lactones related to naphthoquinoneantibiotics

Semmelhack, M. F.; Bodurow, Christina; Baum, M.

doi:10.1016/s0040-4039(01)91000-7

Cited by 74 publications

(16 citation statements)

References 14 publications

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“…Asymmetric oxycarbonylation with (±)-1 (L*)Pd(BF 4 ) 2 Chiral ligand (0.075 mmol) in DCM (1 ml) was added to the solution of Pd(MeCN) 2 Cl 2 (0.05 mmol, 0.05 equiv.) in DCM (1 ml).…”

Section: Resultsmentioning

confidence: 99%

Asymmetric intramolecular Pd(II)-catalysed oxycarbonylation of alkene-1,3-diols

Kapitán¹,

Gracza²

2007

Arkivoc

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The first example of asymmetric oxycarbonylative bicyclisation of racemic pent-4-ene-1,3-diol (±)-1 catalysed by palladium(II) with chiral bis(oxazoline) ligands was investigated. The kinetic resolution of (±)-1 in the presence of chiral catalyst, p-benzoquinone in acetic acid under carbon monoxide atmosphere (balloon) afforded both optically enriched 2,6-dioxabicyclo[3.3.0]octan-3-ones (R,R)-2 and (S,S)-2, respectively.

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“…Asymmetric oxycarbonylation with (±)-1 (L*)Pd(BF 4 ) 2 Chiral ligand (0.075 mmol) in DCM (1 ml) was added to the solution of Pd(MeCN) 2 Cl 2 (0.05 mmol, 0.05 equiv.) in DCM (1 ml).…”

Section: Resultsmentioning

confidence: 99%

Asymmetric intramolecular Pd(II)-catalysed oxycarbonylation of alkene-1,3-diols

Kapitán¹,

Gracza²

2007

Arkivoc

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“…Thepioneering work of Semmelhack and co-workers on palladium(II)-mediated alkoxycarbonylation emerged as an appealing method to simultaneously generate the remaining two rings. [17] Addition of the vinylcerium reagent to 22 gave allylic alcohol 9 in 90 % yield (d.r. = 60:40;S cheme 4).…”

mentioning

confidence: 99%

Pentafulvene for the Synthesis of Complex Natural Products: Total Syntheses of (±)‐Pallambins A and B

Ebner

Carreira

2015

Angew Chem Int Ed

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The first total syntheses of pallambins A and B are enabled by the use of pentafulvene in an unprecedented Diels-Alder reaction. After elaboration of the adduct through chemoselective cyclopropanation, strategic CH insertion affords the dense tetracyclic core of the natural products. 1,3-Dipolar cycloaddition and palladium(II)-catalyzed alkoxycarbonylation were leveraged for the construction of the hexacyclic scaffold en route to both natural products.

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“…The remaining challenge of introducing the tetrahydrofuran and the γ ‐lactone was met next. The pioneering work of Semmelhack and co‐workers on palladium(II)‐mediated alkoxycarbonylation emerged as an appealing method to simultaneously generate the remaining two rings 17. Addition of the vinylcerium reagent to 22 gave allylic alcohol 9 in 90 % yield (d.r.=60:40; Scheme ) 18.…”

Section: Methodsmentioning

confidence: 99%

Pentafulvene for the Synthesis of Complex Natural Products: Total Syntheses of (±)‐Pallambins A and B

Ebner

Carreira

2015

Angewandte Chemie

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The first total syntheses of pallambins Aa nd Ba re enabled by the use of pentafulvene in an unprecedented Diels-Alder reaction. After elaboration of the adduct through chemoselective cyclopropanation, strategic CÀHi nsertion affords the dense tetracyclic core of the natural products.1 ,3-Dipolar cycloaddition and palladium(II)-catalyzed alkoxycarbonylation were leveraged for the construction of the hexacyclic scaffold en route to both natural products.

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Direct synthesis of pyran-lactones related to naphthoquinoneantibiotics

Cited by 74 publications

References 14 publications

Asymmetric intramolecular Pd(II)-catalysed oxycarbonylation of alkene-1,3-diols

Asymmetric intramolecular Pd(II)-catalysed oxycarbonylation of alkene-1,3-diols

Pentafulvene for the Synthesis of Complex Natural Products: Total Syntheses of (±)‐Pallambins A and B

Pentafulvene for the Synthesis of Complex Natural Products: Total Syntheses of (±)‐Pallambins A and B

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