55331-42-5

Upstream product

• 150044-65-8 (+)-1,2-Dehydropinidinol 
• 217823-97-7 (2R,6R)-2-((R)-2-Hydroxy-propyl)-6-methyl-piperidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester 
• 350237-04-6 (2R,2'R,6'R)-(-)-1-(6'-methylpiperidin-2'-yl)-2-(tert-butyldiphenylsilyloxy)propane 
• 913986-11-5 [(E)-(1R,7R)-7-hydroxy-1-methyl-5-oxo-oct-3-enyl]-carbamic acid benzyl ester 
• 913986-13-7 C₁₅H₃₃NOSi 
• 913986-03-5 2-[(R)-1-methyl-but-3-enyl]-isoindole-1,3-dione 
• 913986-05-7 [(R)-1-methyl-but-3-enyl]-carbamic acid benzyl ester 
• 913986-18-2 C₂₃H₃₇NO₄Si 
• 625-31-0 (S)-4-penten-2-ol 
• 7766-48-5 1-iodo-4-pentene 
• 350237-03-5 (2R,4R)-2-(tert-butyldiphenylsilyloxy)-8-nonen-4-amine 
• 350237-01-3 (2R,4S)-2-[(tert-butyldiphenylsilyl)oxy]non-8-en-4-ol 
• 350237-02-4 2-{(R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-propyl]-hex-5-enyl}-isoindole-1,3-dione 
• 1086510-10-2 (-)-epipinidinol 

Relevant academic research and scientific papers

A diastereoselective intramolecular hydroamination approach to the syntheses of (+)-, (±)-, and (-)-pinidinol

A diastereoselective, lanthanocene-catalyzed, intramolecular hydroamination reaction was applied to the preparation of 2,6-disubstituted piperidines. Various metal/ligand arrays in the catalysts were examined using a model substrate to allow optimization of the diastereoselectivity. It was determined that the relationship between metal size and ligand bulk plays an integral role in the transformation. The complex Cp*2NdCH(TMS)2 converted 2-substituted 8-nonen-4-amines to 2,6-disubsituted piperidines with greater than 100: 1 selectivity for the formation of the cis isomer. A short synthesis of pinidinol, an alkaloid isolated from various pine and spruce species, was then carried out to exploit this stereoselective reaction.

A highly efficient synthesis of (-)-pinidinol

A short step synthesis of the bioactive piperidine alkaloid (-)-pinidinol was achieved using a cross metathesis and a reductive amination as the key steps.

Diastereocontrolled reduction of cyclic β-enaminones. A new diastereoselective route to 2,6-disubstituted piperidines

A new diastereoselective synthesis of 2,6-disubstituted piperidinic alkaloids is presented. Three natural compounds, the (-)-pinidinone 1a, the (+)-dihydropinidine 1b and the (-)-pinidinol 1c were prepared from optically pure (6R)-6-methylpiperidin-2-one 2. This method is based on the chemo- and diastereocontrolled reductions of an exocyclic β-enamino ketone.

A general asymmetric route to trans- or cis.2,6-disubstituted piperidine. First total synthesis of (+)-9-epi-6-epipinidinol and (-)- pinidinol

Starting from 1,6-heptadiene, two AD reactions in a stepwise manner lead to the anti-1,5-diol and syn-1,5-diol stereodivergently, which have been converted by aminocyclization into trans- and cis-2,6-disubstituted piperidines (trans- and cis-12), respectively. The first total synthesis of (+)-9-epi-6-epipinidinol (2) and (-)-pinidinol (3) has been achieved from trans- and cis-12.

Toxic Piperidine Alkaloids from Pine (Pinus) and Spruce (Picea) Trees. New Structures and a Biosynthetic Hypothesis

A series of 2,6-disubstituted piperidine alkaloids have been isolated from several Pinus (pine) and Picea (spruce) species and characterized structurally.The pines appear to contain only cis-disubstituted piperidines, while the spruce contain both cis- and trans-disubstituted piperidines.The structural relationships among the alkaloids suggest a plausible biosynthetic scheme and a reason why previous attempts to elucidate the biosynthesis of pinidine failed beyond establishing its polyketide origin.A mixture of alkaloids from needles of Pinus ponderosa proved to be highly teratogenic.The alkaloids might therefore be involved in so-called pine needle abortion which occurs in pregnant range cows which feed on Ponderosa pine needles.