Synthesis of (+)- and (−)-dihydropinidine by diastereoselective dimethylzinc promoted allylation of 2-methyltetrahydropyridine-N-oxide with an allylboronic ester

• The enantiomers of the naturally occurring alkaloid dihydropinidine 1, potential antifeedants against the pine weevil, Hylobius abietis, were prepared by diastereoselective, dimethylzinc mediated addition of pinacolyl 2-propenylboronate 14 to nitrones (R)- and (S)2-methyl tetrahydropyridine-N-oxide 3, prepared from D- and L-alanine, respectively.

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

piperidine alkaloid content

asymmetric-synthesis

2

6-disubstituted piperidines

enantioselective synthesis

spruce

pine

reduction

route

(2s

6r)-dihydropinidine

dihydropinidine

Organic chemistry

Organisk kemi

Chemistry

Publication and Content Type

ref (subject category)

art (subject category)