37209-50-0

Usage

Definition

ChEBI: A sesquiterpenoid commonly found in potatoes.

InChI:InChI=1/C17H26O4/c1-12(18)21-14(2,3)13-6-7-16(5)17(10-13)15(4,11-20-16)8-9-19-17/h8-9,13H,6-7,10-11H2,1-5H3

Upstream product

• 56857-64-8 deacetylphytuberin 
• 108-24-7 acetic anhydride 
• 548757-17-1 1-[(2R,2aR,4aS,7R,8aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-2a,4a-dimethyl-octahydro-1,3-dioxa-cyclobuta[c]inden-7-yl]-ethanol 
• 548757-05-7 (3R,4R,5R)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-seco-12-noreudesman-11-one 
• 548757-04-6 (3R,4R,5R,11S)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-secoeudesman-13-oic acid 
• 54717-69-0 phytuberin lactone 
• 63023-49-4 (3aR,5aS,8R,9aR)-8-(1-Hydroxy-1-methyl-ethyl)-3a,5a-dimethyl-octahydro-benzo[c]furo[3,2-b]furan-2-ol 
• 76193-02-7 1-((1R,2S,5R)-1-Hydroxy-2-hydroxymethyl-5-isopropenyl-2-methyl-cyclohexyl)-ethanone 
• 76192-97-7 (2S,5R)-2-Hydroxymethyl-5-isopropenyl-2-methyl-cyclohexanone 
• 76207-98-2 (1S,3S,6R)-3-Benzyloxymethyl-3,7,7-trimethyl-bicyclo[4.1.0]heptan-2-one 
• 497-62-1 (-)-2-carone 
• 76192-84-2 (5S,6S,9R)-6-Hydroxymethyl-9-(1-hydroxy-1-methyl-ethyl)-4,6-dimethyl-1-oxa-spiro[4.5]dec-3-en-2-one 
• 76192-83-1 (5S,6S,9R)-6-Benzyloxymethyl-9-(1-benzyloxy-1-methyl-ethyl)-4,6-dimethyl-1-oxa-spiro[4.5]dec-3-en-2-one 
• 548757-07-9 (3R,4R,5R)-1,4:3,5-diepoxy-1,2-secoeudesmane-2,11-diol 

Downstream Products

• 56857-64-8 deacetylphytuberin 

Relevant academic research and scientific papers

Synthesis of Phytuberin

The first synthesis of phytuberin, which mimics the proposed biogeneses in critical stages, is described.The synthesis also establishes the absolute configuration.

Synthesis of phytuberin. 4-endo-tet acid-catalyzed cyclization of α-hydroxy epoxides

The total synthesis of phytuberin, a phytoalexin of the Solanum genus, from (-)-α-santonin is reported. The key steps include (a) reductive cleavage of the C-O bond of the γ-lactone with concomitant protection of the C1 double bond, (b) Sharpless stereocontrolled hydroxy-assisted epoxidation of allylic alcohol 6 and simultaneous deprotection of the C1 double bond, (c) a rare 4-endo-tet acid-catalyzed cyclization of an α-hydroxy epoxide, and (d) an unprecedented 4-exo selenocyclization of a homoallylic alcohol.

Total synthesis of (-)-phytuberin

An efficient, total synthesis of the phytoalexin (-)-phytuberin 10 is described starting from (-)-carvone 1.