132185-41-2

Upstream product

• 72505-77-2 4β-Hydroperoxy-4-desoxyvulgarin 
• 3650-22-4 deoxyvulgarin 
• 481-06-1 santonin 
• 1618-78-6 6-epi-α-Santonin 
• 14794-68-4 3-Oxo-5,6αH,4,11βH-eudesman-12,6-olide 
• 4678-03-9 (3S,3aS,5aS,9S,9aS,9bR)-8-Hydroxy-3,5a,9-trimethyl-3a,4,5,5a,8,9,9a,9b-octahydro-3H-naphtho[1,2-b]furan-2-one 
• 6089-71-0 (3S,3aS,5aS,9S,9aS,9bR)-8-Hydroxy-3,5a,9-trimethyl-decahydro-naphtho[1,2-b]furan-2-one 
• 66260-88-6 3β,4β-epoxy-1,1-ethylenedioxy-5,6αH,11βH-eudesman-6,12-olide 
• 132294-82-7 1,1-ethylenedioxy-5,6αH,4,11βH-eudesm-3-en-6,12-olide 
• 132294-81-6 1α,2α-epoxy-3-oxo-5,6αH,4,11βH-eudesman-6,12-olide 
• 132185-39-8 1-oxo-5,6αH,4,11βH-eudesm-2-en-6,12-olide 
• 132204-36-5 2α-bromo-3-oxo-5,6αH,4,11βH-eudesman-6,12-olide 
• 132185-35-4 11,13-dihydro-6β-tuberiferin 
• 132185-38-7 1α-hydroxy-5,6αH,4,11βH-eudesm-2-en-6,12-olide 

Relevant academic research and scientific papers

SYNTHESIS, BIOTRANSFORMATION AND STEREOCHEMISTRY OF 6β-SESQUITERPENE LACTONES: SYNTHESES OF 6β-ARTEPAULIN, 11,13-DIHYDRO-6β-TUBERIFERIN, 5,15-DIHYDRO-6β-OOPODIN, 4-EPI-6β-VULGARIN AND 6β-VULGARIN

6β-Artepaulin, 11,13-dihydro-6β-tuberiferin, 4,15-dihydro-6β-oopodin, 4-epi-6β-vulgarin and 6β-vulgarin were obtained from α-santonin.Stereochemical studies showed that the configuration at C-6 is decisive in the chemical behaviour of the A ring.Biotransformation of 1-oxo-5,6α,4,11βH-eudesm-2-en-6,12-olide with Rhizopus nigricans cultures probed to be a very efficient alternative way to obtain 4-epi-6β-vulgarin, which was then converted to 6β-vulgarin, a convenient starting material for biogenetical studies of pseudoguaianolides.A new 8β-hydroxyl derivative obtained from this biotransformation constitutes a new approach to the synthesis of 8,12-eudesmanolides and other sesquiterpenolides.Molecular structures were determined mainly by mono- and bidimensional nmr experiments.

Microbial Transformations of Sesquiterpenoids: Conversion of Deoxyvulgarin by Rhizopus nigricans and Aspargillus ochraceous

Microbial transformation of the sesquiterpene lactone deoxyvulgarin (2) has been carried out with Aspergillus ochraceous and Rhizopus nigricans cultures.A. ochraceous converted deoxyvulgarin (2) into vulgarin (3) and 11,13-dihydrodouglanin (4).R. nigricans transformed deoxyvulgarin (2) into vulgarin (3), erivanin (6), and 1β-hydroxy-2-oxoeudesm-3-en-6,13-olide (7).Vulgarin (3) was obtained chemically by epoxidation of deoxyvulgarin (2) in one-step process in virtually quantitative yield.A pathway proposed for the conversion of deoxyvulgarin (2) into more functionalized metabolites is discussed.