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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 8
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Original Articles

Stereoselective Reduction of Cyclic 2, 3-Epoxyketones to Trans-2,3-Epoxyalcohols

G. Rücker Pharmazeutisches Institut der Rheinischen Friedrich-Wilhelms-Universität, Bonn; Institut für Pharmazeutische Biologie und Phytochemie der Westfälischen Wilhelms-Universität, Münster
,
H. Hörster Pharmazeutisches Institut der Rheinischen Friedrich-Wilhelms-Universität, Bonn; Institut für Pharmazeutische Biologie und Phytochemie der Westfälischen Wilhelms-Universität, Münster
&
W. Gajewski Pharmazeutisches Institut der Rheinischen Friedrich-Wilhelms-Universität, Bonn; Institut für Pharmazeutische Biologie und Phytochemie der Westfälischen Wilhelms-Universität, Münster
Pages 623-626 | Published online: 05 Dec 2006

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Tapas K. Mandal, Falguni Chattopadhyay, Chayan Guha, Nayim Sepay, Haimanti Mallik & Asok K. Mallik. (2018) Simple Diastereoselective Synthesis of (2S*,2′R*,3′R*,4S*)-2,3′-Diphenylspiro[chroman-3,2′-oxiran]-4-ols and (2S*,2′S*,3′S*,4S*)-2,3′-Diphenylspiro[chroman-3,2′-oxiran]-4-ols. Organic Preparations and Procedures International 50:1, pages 100-107.
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Leo A. Paquette, G. Sabitha, J. S. Yadav, Angelique M. Scheuermann & Rohan R. Merchant. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis 1 15 .
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Richard C. LarockRichard C. Larock & Cristiano Raminelli. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 69 .
Gheorghe-Doru Roiban, Rubén Agudo & Manfred T. Reetz. (2013) Stereo- and regioselectivity in the P450-catalyzed oxidative tandem difunctionalization of 1-methylcyclohexene. Tetrahedron 69:26, pages 5306-5311.
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Sangtae Oh, Daeho Kwon, Woon-Seob Shin, Jungyeob Ham & Seokjoon Lee. (2012) Synthesis of 7,8-epi-Valtrate from (+)-Genipin. Bulletin of the Korean Chemical Society 33:12, pages 4215-4218.
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Louis F. Fieser, Mary Fieser & Tse‐Lok HoTse‐Lok Ho, Mary Fieser, Rick Danheiser, William Roush & Louis Fieser. 2006. Fieser and Fieser's Reagents for Organic Synthesis. Fieser and Fieser's Reagents for Organic Synthesis.
Leo A. Paquette, G. Sabitha & J. S. Yadav. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
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Masaru Hashimoto, Masaharu Sugiura & Shiro Terashima. (2003) Synthetic studies of carzinophilin. Part 3: Synthetic approach toward carzinophilin and successful synthesis of 13-O-desacetyl-12,13-di-O-benzyl-4-O-methylcarzinophilin. Tetrahedron 59:17, pages 3063-3087.
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Christelle Lauret. (2001) Epoxy ketones as versatile building blocks in organic synthesis. Tetrahedron: Asymmetry 12:17, pages 2359-2383.
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Leo A. Paquette. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Denis Gravel & Josée Bordeleau. (1998) Photochemical rearrangement of 2-phenylthio-1,3-cyclohexanediols to deoxysugars. Application to a stereospecific synthesis of (+)-cis-rose oxide. Tetrahedron Letters 39:44, pages 8035-8038.
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Ba V. Nguyen, Zhen-Yu Yang & Donald J. Burton. (1998) A Facile Perfluoroallylation of Olefins. The Journal of Organic Chemistry 63:9, pages 2887-2891.
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K.S Ravikumar & Srinivasan Chandrasekaran. (1996) Chemo- and stereoselective reduction of α,β-epoxyketones with diisopropoxytitanium(III) tetrahydroborate. Tetrahedron 52:27, pages 9137-9142.
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Katja Michael & Horst Kessler. (1996) Michael-type additions in the synthesis of α-O- and -S-2-deoxyglycosides. Tetrahedron Letters 37:20, pages 3453-3456.
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Veejendra K. Yadav & Kamal K. Kapoor. (1996) KF adsorbed on alumina effectively promotes the epoxidation of electron deficient alkenes by anhydrous t-BuOOH. Tetrahedron 52:10, pages 3659-3668.
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Robert W. Murray, Megh Singh, Brian L. Williams & Hazel M. Moncrieff. (1996) Diastereoselectivity in the Epoxidation of Substituted Cyclohexenes by Dimethyldioxirane 1 , 2 . The Journal of Organic Chemistry 61:5, pages 1830-1841.
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Veejendra K. Yadav & Kamal K. Kapoor. (1995) 1,8-diazabicyclo [5.4.0] undec-7-ene: A remarkable base in the epoxidation of α, β-unsaturated-δ-lactones and other enones with anhydrous t-BuOOH. Tetrahedron 51:31, pages 8573-8584.
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H. Künzer & M. Thiel. (1995) A highly stereocontrolled approach to 3-methoxyestra-1,3,5(10),14-tetraen-17α-ol, an important intermediate for the synthesis of C(14)-substituted steroid derivatives. Tetrahedron Letters 36:8, pages 1237-1238.
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Takayo Kawakami, Ikuya Shibata, Akio Baba, Haruo Matsuda & Noboru Sonoda. (1994) Novel synthesis of syn-α,β-epoxy alcohols by diastereoselective carbonyl reduction of α,β-epoxy ketones. Tetrahedron Letters 35:46, pages 8625-8626.
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Philipp Ermert & Andrea Vasella. (2004) Synthesis of a Glucose‐Derived Tetrazole as a New β‐Glucosidase Inhibitor. A New Synthesis of 1‐Deoxynojirimycin. Helvetica Chimica Acta 74:8, pages 2043-2053.
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Dirk Friedrich & Ferdinand Bohlmann. (1988) Total synthesis of various elemanolides. Tetrahedron 44:5, pages 1369-1392.
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Ekkehard WinterfeldtEkkehard Winterfeldt. 1988. Prinzipien und Methoden der Stereoselektiven Synthese. Prinzipien und Methoden der Stereoselektiven Synthese 49 60 .
Gerhard Rücker, Jürgen Kurz & Jutta Friemann. (2006) Über die Struktur eines photochemischen Reaktionsproduktes des Nardosinons. Archiv der Pharmazie 317:8, pages 680-684.
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. 1984. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 24 91 .
A.S. Rao, S.K. Paknikar & J.G. Kirtane. (1983) Recent advances in the preparation and synthetic applications of oxiranes. Tetrahedron 39:14, pages 2323-2367.
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G. + RUECKER, H. + HOERSTER & W. GAJEWSKI. (2016) ChemInform Abstract: STEREOSELECTIVE REDUCTION OF CYCLIC 2,3‐EPOXY KETONES TO TRANS‐2,3‐EPOXY ALCOHOLS. Chemischer Informationsdienst 12:15.
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