112573-32-7

Upstream product

• 106897-35-2 3-[1,3]Dithian-2-yl-4-methoxy-6-((1E,7E,9E)-undeca-1,7,9-trienyl)-pyran-2-one 
• 106897-35-2 3-[1,3]Dithian-2-yl-4-methoxy-6-((1E,7E,9E)-undeca-1,7,9-trienyl)-pyran-2-one 
• 106897-35-2 3-[1,3]Dithian-2-yl-4-methoxy-6-((1E,7E,9E)-undeca-1,7,9-trienyl)-pyran-2-one 
• 84016-84-2 4-methoxy-6-methyl-2-pyrone-3-carboxaldehyde 
• 112722-90-4 3-[1,3]Dithian-2-yl-6-((7E,9E)-2-hydroxy-undeca-7,9-dienyl)-4-methoxy-pyran-2-one 
• 670-28-0 3-Acetyl-4-methoxy-6-methyl-2-pyranone 
• 112495-06-4 3-[1,3]Dithian-2-yl-4-methoxy-6-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pyran-2-one 
• 550346-95-7 (2E,8E,10E)-Dodeca-2,8,10-trienoic acid methoxy-methyl-amide 
• 95019-19-5 (2-[(N-benzylprolyl)amino]benzophenone) 
• 121245-09-8 prosolanapyrone III 
• 88899-60-9 (+)-solanapyrone B 
• 95019-19-5 (6E,8E)-6,8-decadienal and (6Z,8E)-6,8-decadienal 
• 68750-25-4 6-acetoxy-1-hexanal 
• 112513-43-6 4-methoxy-6-methyl-3-vinyl-2-pyrone 

Relevant academic research and scientific papers

Solanapyrones A, B and C, phytotoxic metabolites from the fungus Alternaria solani

On the basis of spectroscopic data and chemical reaction, structures 1, 2 and 3 are proposed for solanapyrones A, B and C, phytotoxins from the fungus Alternaria solani, parasite of potato.

Synthesis of (±)-solanapyrones A and B

In this paper we report the development of a stereoselective IMDA approach to the phytotoxic polyketides (±)-solanapyrones A and B. The stereoselectivity of the key IMDA cycloaddition was optimized by investigating a range of 2,8,10-dodecatrienoic acid derivatives. This established that use of the Weinreb amide led to the desired exo-selectivity and also facilitated construction of the pyrone moiety. A novel approach to the installation of the C-3 formyl group in solanapyrone A is also described.

Total synthesis of (-)-solanapyrone A via enzymatic Diels-Alder reaction of prosolanapyrone

The syntheses of prosolanapyrones I (6) and II (7) via the aldol reactions of pyrone and dienal segments have been achieved in five steps in 31% overall yield for 6 and seven steps in 5% overall yield for 7. An improved synthetic route starting from vinylpyrone 27 provided 7 in 11 steps in 12% overall yield. The enzymatic Diels-Alder reaction of 7 affords (-)- solanapyrone A (1) with high enantioselectivity and with good exo- selectivity, which is difficult to attain by chemical methods. In addition, a crude enzyme preparation from Alternaria solani has been used to perform a kinetic resolution of (±)-3.

Enzymatic Activity Catalysing Exo-selective Diels-Alder Reaction in Solanapyrone Biosynthesis

The crude enzyme from Alternaria solani is able to catalyse the cycloaddition of prosolanapyrone III 6 to the exo adduct solanapyrone A 1 whose optical purity is estimated as 92 +/- 8percent e.e. by HPLC analysis monitored using a CD spectrometer; this enzyme also catalyses the oxidation and cycloaddition of prosolanapyrone II 5 to 1 with 99 +/- 4percent e.e.

SYNTHESIS OF (+/-)-SOLANAPYRONE A

The first synthesis of solanapyrone A (1), a phytotoxin from Alternaria solani, has been completed through the intramolecular Diels-Alder reaction.