Biocatalysis as a useful tool in pheromone synthesis. Enantiomerically pure building blocks from baker's yeast reductions and enzyme catalysed resoluti

• Biocatalytical methods are presented which provide useful building blocks for pheromone synthesis. Examples of the utility of this approach are the preparation of building blocks for the synthesis of stereochemically pure isomers of pine sawfly pheromones and some other pheromones. Enantiom- erically pure ( 98% ee) 2-methyl-1-alkanols 2 were obtained via baker's yeast reduction of suitable α,β-unsaturated aldehydes, and by using lipases from Pseudomonas to effect resolution by transesterification of suitable racemic precursors to 2-methyl-1-alkanols 2 which gave high enantiomeric ratios E > 100. The resolution by esterification mediated by lipase from Candida rugosa of racemic 2-methylalkanoic acids also gave high enantiomeric ratios E> 100 after having improved the reaction conditions by regulating water activity, by choice of the appropriate complimentary substrate alcohol and by adjusting the initial equivalents of the latter present at the start. Also discussed is the separation of diastereomers of diprionol 1, which is naturally occurring in the pine sawfly Neodiprion sertifer, where it is the direct precursor of its pheromone.

Subject headings

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

NATURVETENSKAP  -- Kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences (hsv//eng)

Keyword

Alcohols

Aldehydes

Catalysis

Esterification

Organic acids

Reduction

Substrates

Synthesis (chemical)

Yeast

Candida rugosa

Neodiprion sertifer

Pheromones

Pseudomonas

Biocatalysts

Chemistry

Publication and Content Type

ref (subject category)

art (subject category)