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Jung, Michael E. ; Im, G-Yoon J

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

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

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6 DIBAL = Diisobutylaluminum Hydride
Link

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14 PivCl = pivaloyl chloride = t-Bu-COCl
TBS-Cl = tert-Butyldimethylsilyl Chloride DIBAL = Diisobutylaluminum Hydride TPAP = Tetrapropylammonium Perruthenate NMO = N-Methylmorpholine-N-oxide

15 Ley, Steven V. ; Norman, Joanne; Griffith, William P
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),

16 LiHMDS = Lithium Hexamethyldisilazide = LiN(SiMe3)2

17 Julia Olefination Link

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19 Diimide Reductions

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

21 Weinreb Amide

22 Weinreb Amide General

23 LAB = Lithium amidotrihydroborate = LiH2NBH3

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25 TIPS = Triisopropylsilyl
PCC = Pyridinium Chlorochromate

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27 TFEF = 2,2,2-trifluoroethyl formate = HCO2CH2CF3

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29 Donohoe, Timothy J. ; Thomas, Rhian E. ; Cheeseman, Matthew D
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),

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33 LiTMP = Lithium tetramethylpiperidide
DBB = Di-tert-butylbiphenyl Boc = tert-butyloxycarbonyl = t-BuO-CO

34 Birch Reduction

35 Mechanism of the Birch Reduction

36 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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39 Red-Al is less oxygen sensitive and more soluble than LiAlH4.

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42 Link

43 TMO = trimethylamine-N-oxide
pTSA = p-toluenesulfonic acid

44 DMP = Dess-Martin Periodinane

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56 LiBH4 is a somewhat stronger reducing agent than NaBH4
… But still safer than LiAlH4

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59 Horner-Emmons-Wadsworth Reaction

60 Mechanism of the HEW Reaction

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62 Corey-Bakshi-Shibata Reduction

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