New reagents for stereoselective carbonyl reduction. Improved synthetic route to the primary prostaglandins

Corey, E. J.; Albonico, Sem M.; Koelliker, Urs; Schaaf, Thomas; Varma, Ravi K.

doi:10.1021/ja00735a033

Cited by 204 publications

(40 citation statements)

References 3 publications

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“…[~~~ 351 Further, the small amount of (15R) by-product was easily separated for recycling. Second, using the chiral catalyst 33 (10 mole %) and borane (0.6 mole equivalent) in tetrahydrofuran as solvent at ambient temperature, the 15-ketone 34 was reduced to the (15s) alcohol 35 with 9:l diastereoselecOxazaborolidine 33 is a remarkable catalytic reagent.…”

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confidence: 99%

The Logic of Chemical Synthesis: Multistep Synthesis of Complex Carbogenic Molecules (Nobel Lecture)

Corey

1991

Angew. Chem. Int. Ed. Engl.

364

206

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“Chemical synthesis is uniquely positioned at the heart of chemistry, and its impact on our lives and society is all‐pervasive.” Elias James Corey expresses this opinion in his Nobel Lecture, in which he discusses the origin and development of his contributions leading to the award of the Nobel Prize in chemistry in 1990. His concept of retrosynthetic analysis revolutionized both the practice and teaching of organic chemistry. His application of computers to synthetic planning was pioneering. The numerous synthetic methods developed by him and his co‐workers have proven invaluable in organic synthesis. Finally, the total syntheses carried out in his laboratories—for example, the synthesis of gibberellic acid and of ginkgolide B—are milestones in the breathtaking development of organic synthesis over the last thirty years.

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confidence: 99%

The Logic of Chemical Synthesis: Multistep Synthesis of Complex Carbogenic Molecules (Nobel Lecture)

Corey

1991

Angew. Chem. Int. Ed. Engl.

364

206

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“…The PGF 2a prostaglandins, a kind of the most effective antiglaucoma drugs at present, attracted synthetical chemists' and medicinal chemists' research interest [1][2][3][4]. The aim of the present work of our research group was to search for a convenient and cheap strage to synthesize this kind of prostaglandins.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (±)-(2β-carboxyl-3α-hydroxy-5β-chlorocyclopent- 1α-yl)acetic acid, δ-lactone, C8H9ClO4

Xiong¹,

Liu²,

Zheng³

et al. 2008

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe mixture of the compound 5-chloro-2-oxo-bicycle[2.2.1] heptan-7-oic acid (1 mmol) and m-chloroperoxybenzoic acid (1 mmol) was stirred in dichloromethane (20 ml) for overnight at room temperature followed by column chromatography, and then the title compound was afforded. Crystals appropriate for diffraction data collection were obtained by slow evaporation of an etheyl actate solution at room temperature for 48 hours. Experimental detailsAll H atoms were positioned geometrically and allowed to ride on their parent atoms at distances of d(C-H) = 0.97 or 0.98 Å with U iso = 1.5 Ueq(parent atom). DiscussionThe PGF 2a prostaglandins, a kind of the most effective antiglaucoma drugs at present, attracted synthetical chemists' and medicinal chemists' research interest [1][2][3][4]. The aim of the present work of our research group was to search for a convenient and cheap strage to synthesize this kind of prostaglandins. The title compound was an important intermediate which decided the conformation of the pentacyclo in the prostaglandins structures. In the title crystal structure, the hepta-lactonecycle shows a boat conformation. In the C2−C3−C4−C5−C6 ring, the future pentacyclo in the prostaglandins structures, the C1−C2−C3−O2 torsion angle of −160.4(5)°describes a trans-C2, C3 configuration; the C1−C2−C6−C7 torsion angle of 166.6(5)°describes the trans-C2, C6 configuration; and then, the Cl1−C5−C6−C7 torsion angle of −159.7 (4)°suggests the trans-C5, C6 configuration.

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“…The synthesis started from the Corey aldehyde 13 [27], which was converted to the enone 15 by Horner-Emmons reaction with the phosphonate 14 [28]. Although a geminal difluoride unit has drawn more attention recently in medicinal chemistry, there is no general method to prepare an allyl difluoride from the corresponding enone efficiently [29].…”

Section: Fluorinated Pgf 2α Derivativesmentioning

confidence: 99%

Synthesis and Biological Properties of Novel Fluoroprostaglandin Derivatives: Highly Selective and Potent Agonists for Prostaglandin Receptors

Matsumuraa¹,

Nakanob²,

Moria³

et al. 2004

Chimia

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New reagents for stereoselective carbonyl reduction. Improved synthetic route to the primary prostaglandins

Cited by 204 publications

References 3 publications

The Logic of Chemical Synthesis: Multistep Synthesis of Complex Carbogenic Molecules (Nobel Lecture)

The Logic of Chemical Synthesis: Multistep Synthesis of Complex Carbogenic Molecules (Nobel Lecture)

Crystal structure of (±)-(2β-carboxyl-3α-hydroxy-5β-chlorocyclopent- 1α-yl)acetic acid, δ-lactone, C8H9ClO4

Synthesis and Biological Properties of Novel Fluoroprostaglandin Derivatives: Highly Selective and Potent Agonists for Prostaglandin Receptors

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