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.
CeCl3 promotes the 1,2 reduction of a,b-unsaturated ketones, over the conjugate (1,4) reduction.
TBS-Cl = tert-Butyldimethylsilyl Chloride
DIBAL = Diisobutylaluminum Hydride
TPAP = Tetrapropylammonium Perruthenate
NMO = N-Methylmorpholine-N-oxide
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.
Boukouvalas, John; Wang, Jian-Xin. Structure Revision and Synthesis of a Novel Labdane Diterpenoid from Zingiber ottensii. Organic Letters (2008), 10(16), 3397-3399.
PCC = Pyridinium Chlorochromate
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.
DBB = Di-tert-butylbiphenyl
Boc = tert-butyloxycarbonyl = t-BuO-CO
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.
pTSA = p-toluenesulfonic acid
… But still safer than LiAlH4