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Synthesis of medium and large ring compounds, XXXIX. Stereoselective synthesis of both enantiomers of 13-tetradecanolide by ring enlargement with different chiral building blocks and olfactory comparison with (12R)-(+)- and (12S)-(−)-12-methyl-13-tridecanolide by Philip Kraft; Werner Tochtermann is a Chemistry article available to read on EtoBox.
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## Abstract Starting from a cycloalkanone and the chiral building blocks 2 or 3 both enantiomers of 13‐tetradecanolide (1, n = 14) were prepared by ring‐enlargement reactions. Cycloundeca‐none (4) was α‐alkylated with the protected hydroxy halide 2 derived from (__S__)‐(−)‐methyl lactate. Acid‐catalyzed cyclization, oxidative cleavage of the enol ether double bond by PCC, and reduction of the carbonyl group via a tosylhydrazone led to the (__S__)‐configured target molecule (+)‐8 (98.0% ee), thus indicating the sequence proceeded with clean retention of configuration. Likewise, the naturally occurring (__R__)‐enantiomer (−)‐8 (>99.8% ee) was synthesized from cyclodecanone (9) and the chiral building block 3. Aided by CD conformational analysis the olfactory properties of both enantiomers were compared with those of the regioisomers (12__R__)‐( + )‐ and (12__S__)‐(−)‐12‐methyl‐13‐tridecanolide previously prepared by the same method.
Who reads Synthesis of medium and large ring compounds, XXXIX. Stereoselective synthesis of both enantiomers of 13-tetradecanolide by ring enlargement with different chiral building blocks and olfactory comparison with (12R)-(+)- and (12S)-(−)-12-methyl-13-tridecanolide?
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- Author
- Philip Kraft; Werner Tochtermann
- Publisher
- John Wiley and Sons; Wiley (John Wiley & Sons); VCH Verlagsgesellschaft; Wiley (ISSN 0947-3440)
- Published
- 1995
- Language
- EN
- ISBN
- 9781995199504
- Field
- Chemistry (Physical Sciences)