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Jung, Michael E.; Im, G-Yoon J. Convergent total synthesis of the racemic HIF-1 inhibitor laurenditerpenol. Tetrahed - PowerPoint PPT Presentation


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Jung, Michael E.; Im, G-Yoon J. Convergent total synthesis of the racemic HIF-1 inhibitor laurenditerpenol. Tetrahedron Letters (2008), 49(33), 4962-4964. Luche Reduction. CeCl3 promotes the 1,2 reduction of a , b -unsaturated ketones, over the conjugate (1,4) reduction. Link Link.

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Jung, Michael E.; Im, G-Yoon J. Convergent total synthesis of the racemic HIF-1 inhibitor laurenditerpenol. Tetrahedron Letters (2008), 49(33), 4962-4964.


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Luche Reduction of the racemic HIF-1 inhibitor laurenditerpenol. Tetrahedron Letters (2008), 49(33), 4962-4964.

CeCl3 promotes the 1,2 reduction of a,b-unsaturated ketones, over the conjugate (1,4) reduction.

Link

Link


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DIBAL = Diisobutylaluminum Hydride of the racemic HIF-1 inhibitor laurenditerpenol. Tetrahedron Letters (2008), 49(33), 4962-4964.

Link


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PivCl = pivaloyl chloride = t-Bu-COCl of the racemic HIF-1 inhibitor laurenditerpenol. Tetrahedron Letters (2008), 49(33), 4962-4964.

TBS-Cl = tert-Butyldimethylsilyl Chloride

DIBAL = Diisobutylaluminum Hydride

TPAP = Tetrapropylammonium Perruthenate

NMO = N-Methylmorpholine-N-oxide


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Ley, Steven V.; Norman, Joanne; Griffith, William P.; Marsden, Stephen P. Tetrapropylammonium perruthenate, Pr4N+RuO4-, TPAP: a catalytic oxidant for organic synthesis. Synthesis (1994), (7), 639-66.


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LiHMDS = Lithium Hexamethyldisilazide = LiN(SiMe Marsden, Stephen P. Tetrapropylammonium perruthenate, Pr4N+RuO4-, TPAP: a catalytic oxidant for organic synthesis. Synthesis (1994), (7), 639-66. 3)2


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Julia Olefination Marsden, Stephen P. Tetrapropylammonium perruthenate, Pr4N+RuO4-, TPAP: a catalytic oxidant for organic synthesis. Synthesis (1994), (7), 639-66.

Link


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Diimide Reductions Marsden, Stephen P. Tetrapropylammonium perruthenate, Pr4N+RuO4-, TPAP: a catalytic oxidant for organic synthesis. Synthesis (1994), (7), 639-66.


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Boukouvalas, John; Wang, Jian-Xin. Structure Revision and Synthesis of a Novel Labdane Diterpenoid from Zingiber ottensii. Organic Letters (2008), 10(16), 3397-3399.


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Weinreb Amide Synthesis of a Novel Labdane Diterpenoid from Zingiber ottensii. Organic Letters (2008), 10(16), 3397-3399.


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Weinreb Amide General Synthesis of a Novel Labdane Diterpenoid from Zingiber ottensii. Organic Letters (2008), 10(16), 3397-3399.


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LAB = Lithium amidotrihydroborate = LiH Synthesis of a Novel Labdane Diterpenoid from Zingiber ottensii. Organic Letters (2008), 10(16), 3397-3399. 2NBH3


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TIPS = Triisopropylsilyl Synthesis of a Novel Labdane Diterpenoid from Zingiber ottensii. Organic Letters (2008), 10(16), 3397-3399.

PCC = Pyridinium Chlorochromate


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TFEF = 2,2,2-trifluoroethyl formate = HCO Synthesis of a Novel Labdane Diterpenoid from Zingiber ottensii. Organic Letters (2008), 10(16), 3397-3399. 2CH2CF3


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Donohoe, Timothy J.; Thomas, Rhian E.; Cheeseman, Matthew D.; Rigby, Caroline L.; Bhalay, Gurdip; Linney, Ian D. Flexible Strategy for the Synthesis of Pyrrolizidine Alkaloids. Organic Letters (2008), 10(16), 3615-3618.


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LiTMP = Lithium tetramethylpiperidide D.; Rigby, Caroline L.; Bhalay, Gurdip; Linney, Ian D. Flexible Strategy for the Synthesis of Pyrrolizidine Alkaloids. Organic Letters (2008), 10(16), 3615-3618.

DBB = Di-tert-butylbiphenyl

Boc = tert-butyloxycarbonyl = t-BuO-CO


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Birch Reduction D.; Rigby, Caroline L.; Bhalay, Gurdip; Linney, Ian D. Flexible Strategy for the Synthesis of Pyrrolizidine Alkaloids. Organic Letters (2008), 10(16), 3615-3618.


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Mechanism of the Birch Reduction D.; Rigby, Caroline L.; Bhalay, Gurdip; Linney, Ian D. Flexible Strategy for the Synthesis of Pyrrolizidine Alkaloids. Organic Letters (2008), 10(16), 3615-3618.


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However, the original Birch reduction conditions have some drawbacks, one of which is the use of liquid ammonia as solvent.

The use of other electron donating reagents can permit the use of THF as solvent.


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Red-Al is less oxygen sensitive and more soluble than LiAlH4 drawbacks, one of which is the use of liquid ammonia as solvent..


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Link drawbacks, one of which is the use of liquid ammonia as solvent.


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TMO = trimethylamine-N-oxide drawbacks, one of which is the use of liquid ammonia as solvent.

pTSA = p-toluenesulfonic acid


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DMP = Dess-Martin Periodinane drawbacks, one of which is the use of liquid ammonia as solvent.


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LiBH drawbacks, one of which is the use of liquid ammonia as solvent.4 is a somewhat stronger reducing agent than NaBH4

… But still safer than LiAlH4


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Horner-Emmons-Wadsworth Reaction drawbacks, one of which is the use of liquid ammonia as solvent.


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Mechanism of the HEW Reaction drawbacks, one of which is the use of liquid ammonia as solvent.


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Corey-Bakshi-Shibata Reduction drawbacks, one of which is the use of liquid ammonia as solvent.


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