Total Synthesis

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Tohru Fukuyama - One of the best experts on this subject based on the ideXlab platform.

  • Total Synthesis of (-)-Morphine
    Chemistry: A European Journal, 2017
    Co-Authors: Hirotatsu Umihara, Satoshi Yokoshima, Masayuki Inoue, Tohru Fukuyama
    Abstract:

    The morphinan skeleton was effectively synthesized by an intramolecular Mannich-type reaction. Further transformation led to Total Synthesis of morphine.

  • Total Synthesis of (‐)‐Daphenylline.
    ChemInform, 2016
    Co-Authors: Ryosuke Yamada, Satoshi Yokoshima, Yohei Adachi, Tohru Fukuyama
    Abstract:

    A novel Total Synthesis of (-)-daphenylline, a hexacyclic Daphniphyllum alkaloid, is described.

  • Total Synthesis of daphenylline
    ChemInform, 2016
    Co-Authors: Ryosuke Yamada, Satoshi Yokoshima, Yohei Adachi, Tohru Fukuyama
    Abstract:

    A novel Total Synthesis of (-)-daphenylline, a hexacyclic Daphniphyllum alkaloid, is described.

  • Total Synthesis of (-)-Lepenine
    Journal of the American Chemical Society, 2014
    Co-Authors: Yoshitake Nishiyama, Yuki Han-ya, Satoshi Yokoshima, Tohru Fukuyama
    Abstract:

    The first asymmetric Total Synthesis of lepenine has been accomplished. The Synthesis features a tethered intramolecular Diels-Alder reaction, an intramolecular Mannich reaction, and a Diels-Alder reaction between an ortho-quinone monoketal and ethylene, resulting in stereoselective construction of the unique hexacyclic system.

  • Total Synthesis of dictyodendrins A-E.
    Chemistry-an Asian Journal, 2010
    Co-Authors: Hidetoshi Tokuyama, Kentaro Okano, Hideto Fujiwara, Toshiharu Noji, Tohru Fukuyama
    Abstract:

    A highly efficient Total Synthesis of dictyodendrins A-E was accomplished. The Synthesis features a novel benzyne-mediated one-pot indoline formation/cross-coupling sequence for the construction of a highly substituted key indoline intermediate. Peripheral substituents were introduced onto this intermediate in a modular fashion to complete the Total Synthesis of dictyodendrins A-E.

Masahisa Nakada - One of the best experts on this subject based on the ideXlab platform.

  • Collective Total Synthesis of PPAPs: Total Synthesis of clusianone via intramolecular cyclopropanation.
    Natural Product Communications, 2020
    Co-Authors: Masahiro Uwamori, Masahisa Nakada
    Abstract:

    The Total Synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence, which has been utilized for the Total syntheses of nemorosone, garsubellin A, and hyperforin: intramolecular cyclopropanation, formation of a geminal dimethyl group, and regioselective ring opening of cyclopropane. Further elaboration, including chemo- and stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains, was employed to complete the Total Synthesis ofclusianone.

  • Stereoselective Total Synthesis of garsubellin A
    The Journal of Antibiotics, 2013
    Co-Authors: Masahiro Uwamori, Masahisa Nakada
    Abstract:

    The stereoselective Total Synthesis of garsubellin A is described. The Total Synthesis was achieved through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence: intramolecular cyclopropanation, formation of a germinal dimethyl group, and regioselective ring opening of cyclopropane. To complete the Total Synthesis of garsubellin A, chemo- and stereoselective hydrogenation to generate the C8 stereogenic center is followed by the formation of the fused tetrahydrofuran ring by a regioselective epoxide-opening reaction with C3 ketone, and finally cross metathesis to construct two prenyl groups.

  • Stereoselective Total Synthesis of nemorosone.
    Journal of Organic Chemistry, 2012
    Co-Authors: Masahiro Uwamori, Aya Saito, Masahisa Nakada
    Abstract:

    The highly stereoselective Total Synthesis of nemorosone via a new approach to the bicyclo[3.3.1]nonane-2,4,9-trione core which features intramolecular cyclopropanation of an α-diazo ketone, stereoselective alkylation at the C8 position, and regioselective ring-opening of cyclopropane is described. The Total Synthesis of nemorosone includes chemo- and stereoselective hydrogenation directed by the internal alkene.

  • enantioselective Total Synthesis of digitoxigenin
    Tetrahedron Letters, 2007
    Co-Authors: Masahiro Honma, Masahisa Nakada
    Abstract:

    Abstract An enantioselective Total Synthesis of (+)-digitoxigenin is described. This Total Synthesis is accomplished in a convergent manner using two chiral fragments prepared via the catalytic asymmetric intramolecular cyclopropanation and baker’s yeast mediated reduction developed by us, respectively. This convergent Synthesis would be useful for preparing some new derivatives of digitoxigenin for SAR studies and could be applied for the Total Synthesis of other cardenolides left unprepared.

  • Enantioselective Total Synthesis of (+)-digitoxigenin
    Tetrahedron Letters, 2007
    Co-Authors: Masahiro Honma, Masahisa Nakada
    Abstract:

    Abstract An enantioselective Total Synthesis of (+)-digitoxigenin is described. This Total Synthesis is accomplished in a convergent manner using two chiral fragments prepared via the catalytic asymmetric intramolecular cyclopropanation and baker’s yeast mediated reduction developed by us, respectively. This convergent Synthesis would be useful for preparing some new derivatives of digitoxigenin for SAR studies and could be applied for the Total Synthesis of other cardenolides left unprepared.

Masahiro Honma - One of the best experts on this subject based on the ideXlab platform.

  • enantioselective Total Synthesis of digitoxigenin
    Tetrahedron Letters, 2007
    Co-Authors: Masahiro Honma, Masahisa Nakada
    Abstract:

    Abstract An enantioselective Total Synthesis of (+)-digitoxigenin is described. This Total Synthesis is accomplished in a convergent manner using two chiral fragments prepared via the catalytic asymmetric intramolecular cyclopropanation and baker’s yeast mediated reduction developed by us, respectively. This convergent Synthesis would be useful for preparing some new derivatives of digitoxigenin for SAR studies and could be applied for the Total Synthesis of other cardenolides left unprepared.

  • Enantioselective Total Synthesis of (+)-digitoxigenin
    Tetrahedron Letters, 2007
    Co-Authors: Masahiro Honma, Masahisa Nakada
    Abstract:

    Abstract An enantioselective Total Synthesis of (+)-digitoxigenin is described. This Total Synthesis is accomplished in a convergent manner using two chiral fragments prepared via the catalytic asymmetric intramolecular cyclopropanation and baker’s yeast mediated reduction developed by us, respectively. This convergent Synthesis would be useful for preparing some new derivatives of digitoxigenin for SAR studies and could be applied for the Total Synthesis of other cardenolides left unprepared.

Rodrigo B Andrade - One of the best experts on this subject based on the ideXlab platform.

  • Total Synthesis of desmethyl macrolide antibiotics
    Synlett, 2015
    Co-Authors: Rodrigo B Andrade
    Abstract:

    Macrolide antibiotics occupy a special place in the history of organic chemistry and medicine. This account chronicles the evolution of our approach that ultimately led to the successful Total syntheses of four desmethyl (i.e., Me → H) analogues of telithromycin, a semisynthetic derivative of the flagship macrolide antibiotic, erythromycin. 1 Introduction 2 Project Rationale and Retrosynthetic Analysis 3 Lessons Learned from the Total Synthesis of 4,8,10-Tridesmethyl Telithromycin 4 Total Synthesis of 4,10-Didesmethyl Telithromycin 5 Total Synthesis of 4,8-Didesmethyl Telithromycin 6 Total Synthesis of 4-Desmethyl Telithromycin 7 Biological Evaluation of Desmethyl Telithromycin Analogues 8 Concluding Remarks

  • Total Synthesis of (+)-crocacin C.
    Bioorganic & Medicinal Chemistry, 2010
    Co-Authors: Gopal Sirasani, Tapas Paul, Rodrigo B Andrade
    Abstract:

    Abstract Two approaches toward the Total Synthesis of cytotoxic polyketide natural product (+)-crocacin C ( 1 ) are described. The first approach, which was ultimately unsuccessful, was replaced altogether with a second that afforded target 1 in 10 linear steps from commercially available Evans’ chiral propionimide (5% overall yield). No protecting groups were utilized in the Total Synthesis of 1 .

Gowravaram Sabitha - One of the best experts on this subject based on the ideXlab platform.