83113-69-3

Upstream product

• 55784-90-2 epioxylubimin 
• 55784-90-2 3-hydroxylubimin 
• 55784-90-2 (+/-)-oxylubimin 
• 55784-90-2 (+/-)-10-epioxylubimin 
• 101415-98-9 (2RS,5RS,8SR,9SR,10RS)-9-methoxymethoxy-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-en-8-ol 
• 129165-36-2 Methanesulfonic acid 2-((2R,5S,8R,9R,10S)-6-formyl-8,9-bis-methoxymethoxy-10-methyl-spiro[4.5]dec-6-en-2-yl)-propyl ester 
• 101416-00-6 Methanesulfonic acid (2S,5S,8R,9R,10S)-8,9-bis-methoxymethoxy-6,10-dimethyl-spiro[4.5]dec-6-en-2-yl ester 
• 101467-36-1 (2RS,5RS,8SR,9SR,10RS)-8,9-bis(methoxymethoxy)-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-ene 
• 101415-97-8 (2RS,5RS,9SR,10RS)-9-methoxymethoxy-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-en-8-one 
• 101415-96-7 (2RS,5RS,9SR,10RS)-9-hydroxy-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-en-8-one 
• 101415-99-0 (2RS,5RS,8SR,9SR,10RS)-8,9-bis(methoxymethoxy)-6,10-dimethyl-spiro<4.5>dec-6-en-2-ol 
• 101416-01-7 diethyl(2RS,5SR,8RS,9RS,10SR)-8,9-bis(methoxymethoxy)-6,10-dimethylspiro<4.5>dec-6-en-2-ylmalonate 
• 101416-04-0 (2RS,5SR,9RS,10SR)-6-hydroxymethyl-2-(2-mesyloxy-1-methylethyl)-8,9-bis(methoxymethoxy)-10-methylspiro<4.5>dec-6-ene 
• 101416-06-2 (2RS,5SR,6SR,8RS,9RS,10SR)-2-(2-mesyloxy-1-methylethyl)-7,8-bis(methoxymethoxy)-10-methylspiro<4.5>decane-6-carbaldehyde 

Downstream Products

• 61263-55-6 3-hydroxy-15-dihydrolubimin 
• 55784-90-2 10-epi-3-hydroxylubimin 
• 55784-90-2 oxylubimin 
• 61263-55-6 Dihydrooxylubimin 
• 61263-55-6 10-epi-3-hydroxy-15-dihydrolubimin 
• 55784-90-2 (+/-)-oxylubimin 
• 55784-90-2 (+/-)-10-epioxylubimin 

Relevant academic research and scientific papers

Total Synthesis of (+/-)-Lubimin and (+/-)-Oxylubimin

The total synthesis of the title compounds, examples of the spirovetivane type of phytoalexins in the genus Solanum, by transformation of (+/-)-15-norsolavetivone and its derivatives, is described.

1H NMR Study of the Stereochemistry of Lubimin and Related Vetispirane Sesquiterpenoids

The stereochemistry at C-2 and C-10 in lubimin, 15-dihydrolubimin and 3-hydroxylubimin derivatives has been investigated by 1H NMR spectroscopy.Using parent compounds and acetyl derivatives (24 compounds) definitive spectroscopic assignments have been made.Nine oxidised derivatives (2- and 3-keto functionalisation) have also been investigated.The usefulness of diagnostic features in the spectra are illustrated and the conformational homogeneity of the series verified.

A STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-OXYLUBIMIN

(+/-)-Oxylubimin (1), the highest oxidized spirovetivane-type phytoalexin, was totally synthesized with high stereoselectivity using a novel method for α'-hydroxylation of α,β-unsaturated ketones.

Total Synthesis of (+/-)-Lubimin and (+/-)-Oxylubimin. II. Transformation of (+/-)-15-Norsolavetivanes into (+/-)-Lubimin, (+/-)-Oxylubimin, and Related Compounds

The transformation of (+/-)-15-norsolavetivone and related compounds, into (+/-)-lubimin and (+/-)-oxylubimin, which constitutes the total synthesis of these highly oxygenated spirovetivane phytoalexins, is described.

Structure of Epilubimin, Epioxylubimin, and Isolubimin, Spirovetivane Stress Metabolites in Diseased Potato

The isolation and structure elucidation of the title spirovetivane sesquiterpenes, stress metabolites produced in diseased potato tubers, are described.