Total synthesis of carboprostacyclin, a stable and biologically active analogue of prostacyclin (PGI2)

Nicolaou, K. C.; Sipio, W. J.; Magolda, Ronald L.; Seitz, Steven P.; Barnette, W. E.

doi:10.1039/c39780001067

Cited by 51 publications

(8 citation statements)

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“…Found: C, 84.65; , 7.18. Hexacyclo[6.5.1.02'7.03,11.04'9.010 '14]tetradec-12-en-5-ol (9). To a stirred solution of 8 (500 mg, 2.5 mmol) in methanol (25 mL) was added sodium borohydride (500 mg, 12.5 mmol) in three portions in a period of 3 min.…”

mentioning

confidence: 99%

Synthesis of 2',3'-dideoxyuridine via deoxygenation of 2',3'-O-(methoxymethylene)uridine

Shiragami¹,

Irie²,

Shirae³

et al. 1988

J. Org. Chem.

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mentioning

confidence: 99%

Synthesis of 2',3'-dideoxyuridine via deoxygenation of 2',3'-O-(methoxymethylene)uridine

Shiragami¹,

Irie²,

Shirae³

et al. 1988

J. Org. Chem.

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“…Today, this model is even more desired, and almost obligatory, due to the strong emphasis placed on translational and applied research in academia. In our group, we have adopted and championed this paradigm from the 1970s with our work on prostaglandins, 170,[203][204][205][206][207][208][209][210][211][212][213][214] prostacyclins, [208][209][210][215][216][217][218][219][220][221][222][223][224][225][226][227][228][229][230][231][232] thromboxanes 210,233,234 and other eicosanoids. We continued to intensify our interfacing of target-oriented synthesis with analogue design, synthesis and biological evaluation throughout the years 169 until the 2000s when we became fully committed to translational research in partnership with academic colleagues and other experts from the pharmaceutical and biotechnology industries.…”

Section: Discussionmentioning

confidence: 99%

Total Synthesis Endeavors and Their Contributions to Science and Society: A Personal Account

Nicolaou

Rigol

2019

CCS Chem

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The advent of organic synthesis in the 19th century, serendipitous as it was, set in motion a revolution in science that continues to evolve into increasing levels of sophistication and to expand into new domains of science and technology for the benefits of science and society. Its evolution was always driven by the challenges posed by natural products, whose structures were becoming increasingly complex and diverse. In response to these challenges, synthetic organic chemists were prompted to sharpen their art to reach their target molecules, whose structures were often confirmed only after their synthesis in the laboratory through the art and science of total synthesis. The latter became the “locomotive” and the “flagship” of organic synthesis, for through this practice novel synthetic methods were discovered and invented, and also tested for their generality, applicability, and scope with regard to molecular complexity and diversity. The purpose of total synthesis has also evolved over the years to include aspects beyond the synthesis of the molecule and confirmation of its structure. In this article, we briefly review the evolution of total synthesis in terms of its power and reach and demonstrate its current state of the art that combines fundamentals with translational aspects through examples from our laboratories. The highlighted examples reflect the newly emerged paradigm of the discipline that includes—in addition to the total synthesis of the target molecule—structural elucidations, method discovery and development, design, synthesis, and biological evaluation of analogues for biology and medicine, and training of young students, preparing them for academic and industrial careers in the various disciplines that require knowledge and skills to practice the central science of chemical synthesis. Such disciplines include chemical biology, drug discovery and development, materials science and nanotechnology, and other endeavors whose fundamentals depend and rely on the structure of the molecule and its synthesis.

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“…Reaction of l-heptene-d-dj (5) with 1 was carried out under pseudo-first-order conditions (18 M excess of 5) at 130 °C as described above. Samples were withdrawn at 1-3-h intervals, quenched by cooling to -20 °C, diluted with benzene, passed through a layer of silica gel, washed with water, dried (anhydrous MgS04), and evaporated.…”

Section: Methodsmentioning

confidence: 99%

“…The reactions with monodeuterated heptene (5) were carried out for the intramolecular comparison and with dideuterated heptene (6) for the intermolecular comparison with 4. The separate primary and secondary isotope effects were calculated by using eq 1 and 2 (see Experimental Section). The solution of these equations gave kH'/kO' = 2.16 ± 0.08 and kK"/kp" = 1.05 ± 0.04 values, respectively.…”

mentioning

confidence: 99%

Mechanism of the dimethyl mesoxalate-alkene ene reaction. Deuterium kinetic isotope effects

Achmatowicz¹,

Szymoniak²

1980

J. Org. Chem.

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Total synthesis of carboprostacyclin, a stable and biologically active analogue of prostacyclin (PGI2)

Cited by 51 publications

References 0 publications

Synthesis of 2',3'-dideoxyuridine via deoxygenation of 2',3'-O-(methoxymethylene)uridine

Synthesis of 2',3'-dideoxyuridine via deoxygenation of 2',3'-O-(methoxymethylene)uridine

Total Synthesis Endeavors and Their Contributions to Science and Society: A Personal Account

Mechanism of the dimethyl mesoxalate-alkene ene reaction. Deuterium kinetic isotope effects

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