Key Reaction Sequence

1
(No Transcript)
2
Key Reaction Sequence

• reduction of ketone
• quasi-Favorskii rearrangement
• reduction of aldehyde
• conversion of alcohol to iodide
• reductive deiodinination

3
Background
The Favorskii Rearrangement
4
Background
The Favorskii Rearrangement

• generally, a-haloketones ? esters
• often used for ring contractions

5
Background
The Quasi-Favorskii Rearrangement
6
Background
Dicyclohexylcarbodiimide (DCC)
electrophilic carbon
basic lone pair
7
Background
Dicyclohexylcarbodiimide (DCC)
8
Background
Dicyclohexylcarbodiimide methiodide (DCCMeI)
9
Key Reaction Sequence

• reduction of ketone
• quasi-Favorskii rearrangement
• reduction of aldehyde
• conversion of alcohol to iodide
• reductive deiodinination

10
Reduction of the Ketone
11
Quasi-Favorskii Rearrangement
12
Quasi-Favorskii Rearrangement
13
Quasi-Favorskii Rearrangement
14
Quasi-Favorskii Rearrangement
15
Aldehyde Reduction
16
Iododehydroxylation
17
Reductive Deiodination
18
Summary
Overall transformation

• conversion of bicyclo4.2.1nonan-7-one ?
  bicyclo4.2.0octane

19
Summary
Functional group conversions

• LAH reduction
• Favorskii quasi-Favorskii rearrangements
• iododehydroxylation
• reductive deiodination

20
Summary
Reagents

• LAH
• DCC
• DCCMeI