Organic synthesis
Kamil Paruch
Masaryk University, Brno
X: often SO2
J. Org. Chem. 1960, 25, 1481.
• two s bonds which terminate at a single atom are made or broken in concert
trans:cis = 60:40
(difficult to separate)
trans
Tetrahedron Lett. 1973, 4669.
vs.
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colombiasin A
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colombiasin A
Angew. Chem. Int. Ed. 2001, 40, 2482.
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ibogamin
Org. Lett. 2000, 2, 2373.
Beckmann rearrangement
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cephalotaxin
J. Am. Chem. Soc. 1999, 121, 10264.
amination of allyl acetates
Heck rxn
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damsin J. Am. Chem. Soc. 1976, 98, 3379.
step 3. : reduction of benzylalcohol
step 1. : esterification
step 2. : reduction of benzylalcohol
step 2. : selective oxidation
of primary OH
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reserpine
J. Am. Chem. Soc. 1985, 107, 4072.
chemoselective reduction
of amide to amine
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Ramberg-Bäcklund rearrangementKamil Paruch Organic Synthesis C4450
Can. J. Chem. 2000, 78, 1060.
• can be applied to construct both small and large rings
J. Am. Chem. Soc. 1971, 93, 4516.
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