Synthesis of decalin type chiral synthons based on enzymatic function

Area of Science:

• Organic Chemistry
• Biocatalysis
• Asymmetric Synthesis

Background:

• Naphthalene derivatives are important scaffolds in organic synthesis.
• Developing efficient methods for enantioselective synthesis is crucial.
• Enzymatic transformations offer a green and selective approach.

Purpose of the Study:

• To explore enzymatic monobenzoylation of naphthalene derivatives.
• To achieve high enantiomeric excess (ee) in enzymatic reactions.
• To synthesize optically active naphthalene derivatives.

Main Methods:

• Enzymatic monobenzoylation using vinyl benzoate in organic solvent.
• Enzymatic hydrolysis of acetoxybenzylidene acetals.
• Determination of enantiomeric excess (ee) using chromatographic methods.

Main Results:

• Enzymatic monobenzoylation yielded optically active diols and monobenzoates with 11-49% ee.
• Enzymatic hydrolysis of (+/-)-25d, e provided (10aS)-25d, e with >90% ee.
• The 90% ee of (10aS)-25e was converted to 90% ee of (8aS)-1.

Conclusions:

• Enzymatic methods are effective for the enantioselective synthesis of naphthalene derivatives.
• High enantioselectivity can be achieved through optimized enzymatic hydrolysis.
• This study provides a pathway for accessing optically pure naphthalene compounds.