Total synthesis of riccardin C and (±)-cavicularin via Pd-catalyzed Ar–Ar cross couplings

Harada, Kenichi; Makino, Kosho; Shima, Naoki; Okuyama, Haruka; Esumi, Tomoyuki; Kubo, Miwa; Hioki, Hideaki; Asakawa, Yoshinori; Fukuyama, Yoshiyasu

doi:10.1016/j.tet.2013.06.064

Cited by 20 publications

(11 citation statements)

References 32 publications

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“…Cavicularin has captured the attention of synthetic chemists, and the groups of Harrowven, [12] Baran, [13] Fukuyama, [14] Suzuki, [15] and our own [16] have reported syntheses of cavicularin. The synthesis by Suzuki and coworkers featured an elegant use of a chiral sulfoxide auxiliary for the synthesis of (À)-cavicularin.…”

mentioning

confidence: 99%

Enantioselective and Regioselective Pyrone Diels–Alder Reactions of Vinyl Sulfones: Total Synthesis of (+)‐Cavicularin

Zhao

Beaudry

2014

Angew Chem Int Ed

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confidence: 99%

Enantioselective and Regioselective Pyrone Diels–Alder Reactions of Vinyl Sulfones: Total Synthesis of (+)‐Cavicularin

Zhao

Beaudry

2014

Angew Chem Int Ed

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“…Cavicularin has captured the attention of synthetic chemists, and the groups of Harrowven,12 Baran,13 Fukuyama,14 Suzuki,15 and our own16 have reported syntheses of cavicularin. The synthesis by Suzuki and co‐workers featured an elegant use of a chiral sulfoxide auxiliary for the synthesis of (−)‐cavicularin.…”

Section: Methodsmentioning

confidence: 99%

Enantioselective and Regioselective Pyrone Diels–Alder Reactions of Vinyl Sulfones: Total Synthesis of (+)‐Cavicularin

Zhao

Beaudry

2014

Angewandte Chemie

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The total synthesis of (+)-cavicularin is described. The synthesis features an enantio-and regioselective pyrone Diels-Alder reaction of a vinyl sulfone to construct the cyclophane architecture of the natural product. The Diels-Alder substrate was prepared by a regioselective one-pot threecomponent Suzuki reaction of a non-symmetric dibromoarene.Scheme 1. Enantioselective Diels-Alder reactions of a-pyrones. BINOL = 1,1'-bi-2-naphthyl, Tf = trifluoromethanesulfonyl.Scheme 2. Retrosynthetic analysis of (+)-cavicularin. Scheme 3. Reagents and Conditions: a) [Pd(PPh 3 ) 4 ], K 3 PO 4 , DMSO, 70 8C, 52 %; b) [Pd(PPh 3 ) 4 ], K 3 PO 4 , KBr, dioxane, H 2 O, 55 8C; c) Grubbs II catalyst, CH 2 Cl 2 , 508C, 95 %; d) H 2 (600 psi), Pd/C, EtOAc, 60 8C, 87 %. pin = pinacolato.

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“…Secondly, 1 is the first natural compound that displays optical activity solely derived from the atropisomerism, and where the absolute configuration has remained unassigned 1. 4…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Determination of the Absolute Configuration of Cavicularin by a Symmetrization/Asymmetrization Approach

2013

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Molekül unter Spannung: Die asymmetrische Totalsynthese samt stereochemischer Bestimmung von (−)‐Cavicularin, einer Verbindung mit hoch gespanntem Polycyclophan‐Ringsystem, beruhte auf 1) einer Makrocyclisierung über eine SNAr‐Reaktion, 2) einer gruppenselektiven Reaktion, um die Chiralitätsebene hoch stereoselektiv festzulegen, und 3) einer radikalischen transannularen Kupplung zur Bildung des gespannten Ringsystems.

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Total synthesis of riccardin C and (±)-cavicularin via Pd-catalyzed Ar–Ar cross couplings

Cited by 20 publications

References 32 publications

Enantioselective and Regioselective Pyrone Diels–Alder Reactions of Vinyl Sulfones: Total Synthesis of (+)‐Cavicularin

Enantioselective and Regioselective Pyrone Diels–Alder Reactions of Vinyl Sulfones: Total Synthesis of (+)‐Cavicularin

Enantioselective and Regioselective Pyrone Diels–Alder Reactions of Vinyl Sulfones: Total Synthesis of (+)‐Cavicularin

Synthesis and Determination of the Absolute Configuration of Cavicularin by a Symmetrization/Asymmetrization Approach

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