Lithium borohydride (LiBH4) is a useful reducing agent, as it is more selective than LiAlH4 but less selective than NaBH4. Specifically, LiBH4 will reduce esters, but it will not reduce amides. This selectivity is frequently employed by synthetic organic chemists. For example, during a synthesis of (-)-croalbinecine, a natural product with cytotoxic properties, compound 1 was converted to compound 3, as shown below (J. Org. Chem. 2000, 65, 9249-9251). Draw the structures of 2 and 3. CO₂Et но. Ph OCH 1) Excess LiBH4 2) H₂O 2 1) Excess NaH, excess PhCH₂Br, DMF 2) H₂, Lindlar's catalyst 3
Lithium borohydride (LiBH4) is a useful reducing agent, as it is more selective than LiAlH4 but less selective than NaBH4. Specifically, LiBH4 will reduce esters, but it will not reduce amides. This selectivity is frequently employed by synthetic organic chemists. For example, during a synthesis of (-)-croalbinecine, a natural product with cytotoxic properties, compound 1 was converted to compound 3, as shown below (J. Org. Chem. 2000, 65, 9249-9251). Draw the structures of 2 and 3. CO₂Et но. Ph OCH 1) Excess LiBH4 2) H₂O 2 1) Excess NaH, excess PhCH₂Br, DMF 2) H₂, Lindlar's catalyst 3
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Chapter1: Chemical Foundations
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Transcribed Image Text:Lithium borohydride (LiBH4) is a useful reducing agent, as it is more selective than LIAIH4 but less selective than NaBH4. Specifically,
LiBH4 will reduce esters, but it will not reduce amides. This selectivity is frequently employed by synthetic organic chemists. For
example, during a synthesis of (-)-croalbinecine, a natural product with cytotoxic properties, compound 1 was converted to compound
3, as shown below (J. Org. Chem. 2000, 65, 9249-9251). Draw the structures of 2 and 3.
CO₂Et
но-
1
-N
Ph
1) Excess LiBH4
2) H₂O
OCH 3
2
1) Excess NaH,
excess PhCH₂Br,
DMF
2) H₂, Lindlar's catalyst
3
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