88899-61-0

Usage

InChI:InChI=1/C18H22O4/c1-11-7-8-12-5-3-4-6-13(12)17(11)16-9-15(21-2)14(10-19)18(20)22-16/h7-13,17H,3-6H2,1-2H3/t11-,12+,13+,17+/m0/s1

Upstream product

• 95019-19-5 (6E,8E)-6,8-decadienal and (6Z,8E)-6,8-decadienal 
• 112722-90-4 3-[1,3]Dithian-2-yl-6-((7E,9E)-2-hydroxy-undeca-7,9-dienyl)-4-methoxy-pyran-2-one 
• 84016-84-2 4-methoxy-6-methyl-2-pyrone-3-carboxaldehyde 
• 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 
• 95019-19-5 (2-[(N-benzylprolyl)amino]benzophenone) 
• 154584-30-2 prosolanapyrone I 
• 88899-60-9 (-)-solanapyrone B 
• 121245-09-8 prosolanapyrone III 
• 154584-31-3 prosolanapyrone II 
• 106897-34-1 3-[1,3]Dithian-2-yl-4-methoxy-6-methyl-pyran-2-one 
• 112495-00-8 3-(1-hydroxyethyl)-4-methoxy-6-methyl-2-pyrone 
• 112513-43-6 4-methoxy-6-methyl-3-vinyl-2-pyrone 

Downstream Products

• 106897-33-0 C₃₆H₄₀O₁₁ 

Relevant academic research and scientific papers

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.

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.