1351-48-0

Upstream product

• 67-56-1 methanol 
• 144067-18-5 Acetic acid (6Z,8Z,10E)-(3S,3aS,11aS)-3,6,10-trimethyl-2-oxo-2,3,3a,4,5,11a-hexahydro-cyclodeca[b]furan-7-yl ester 
• 72505-77-2 Peroxyvulgarin 
• 3650-22-4 Deoxyvulgarin 
• 16981-97-8 11,13-didehydrovulgarin 
• 14794-68-4 3-Oxo-5,6αH,4,11βH-eudesman-12,6-olide 
• 1618-78-6 6-epi-α-Santonin 
• 481-06-1 santonin 
• 3650-22-4 deoxyvulgarin 
• 132185-38-7 1α-hydroxy-5,6αH,4,11βH-eudesm-2-en-6,12-olide 
• 66428-34-0 (11S)-3α,4α-Epoxy-1α-hydroxyeudesmano-13,6α-lactone 
• 16886-42-3 1α-hydroxy-5α,6β,7α,11βH-eudesm-3-en-6,13-olide 
• 3835-53-8 (11S)-3α,4α-Epoxy-1oxoeudesmano-13,6α-lactone 
• 72505-77-2 4β-Hydroperoxy-4-desoxyvulgarin 

Downstream Products

• 132185-41-2 6β-vulgarin 
• 7715-89-1 11,13-dihydrosantamarin 

Relevant academic research and scientific papers

A NEW COMPONENT OF Artemisia fragrans

A new component C15H22O3, has been isolated from the epigeal part of Artemisia fragrans.On the basis of chemical transformations and spectral characteristics it has been established that it has the structure of 1α-hydroxy-5,7αH,6,11βH-eudesm-3,4-en-6,12-olide (I).

Transformations of Some Sesquiterpene Lactones by Filamentous Fungi and Cytotoxic Evaluations

Biotransformation is an economically and ecologically viable technology which has been used to modify the structures of many classes of biologically active products. Some fungi may be useful for the biotransformation of sesquiterpene lactones (SLs), leading to unusual structural changes that modify their biological activities, and other transformations mimic their biosynthetic pathways, generating evidences for the proposed biogenesis. Eight filamentous fungi were screened for their ability to transform different SLs (1?–?9), and microbial reactions yielded compounds 10?–?17, which in turn have been isolated as natural products, thus mimicking their biosynthesis. Their structures were identified based on NMR and MS spectroscopic analyses. The cytotoxicities of SLs 1, 4, 6, 7 and 9, and their biotransformed produts (10, 14, 15 and 17) against human cancer cell lines U251 (glia), PC3 (prostate), K562 (leukemia), HCT-15 (colon), MCF7 (breast), and SKLU-1 (lung), were determined, confirming that the presence of Michael acceptor is an important feature for the bioactivity.

Partial synthesis of germacranolides with pyran and furan-type rings

Pathways to synthesize germacranolides with ether bridges between C1 and C5 or C3 and C10 were described. A joint precursor was prepared using a readily available and inexpensive compound as starting material. The key step in the preparation of dihydropyranone-germacranolides proved to be a one-pot procedure involving several transformation, induced by the iodotrimethylsilane/acetonitrile system.

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.

BIOGENETIC-TYPE SYNTHESIS OF VULGARIN AND PEROXYVULGARIN

The eudesmanolides vulgarin and peroxyvulgarin were obtained via a biogenetic-type route that involved photo-oxygenation of 1-oxo-5αH,6,11βH-eudesm-3-en-6,12-olide.The α-face singlet oxygen (1O2) attack resulted in the production of peroxyvulgarin as the major product.Stannous chloride reduction of that compound readily yielded vulgarin.These two compounds, vulgarin and peroxyvulgarin, were isolated from Artemisia abyssinica.Key Word Index- Artemisia abyssinica; Compositae; vulgarin; peroxyvulgarin; photo-oxygenation; biogenetic; 1-oxo-5αH,6,11βH-eudesm-3-en-6,12-olide.

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.

Evidence for the Biogenesis of 1α-Hydroxy-trans-eudesmanolides

1-epi-Gallicin (10), a modified germacranolide, has been prepared from gallicin (12).A biogenetic-type cyclization of (10) afforded 1α-hydroxy-trans-eudesmanolides.The mechanism and the stereospecificity of the reaction are discussed in terms of a preferred reacting conformation.The possible biogenetic significance of the process is outlined.