2225-79-8

Upstream product

• 70868-32-5 Methanesulfonic acid (1aR,4R,5R,5aS,8S,8aS,10aR)-4,8,10a-trimethyl-7-oxo-dodecahydro-1,6-dioxa-cyclopenta[a]cyclopropa[e]cyclodecen-5-yl ester 
• 70868-30-3 (1aR,4R,5R,5aS,8S,8aS,10aR)-5-Hydroxy-4,8,10a-trimethyl-decahydro-1,6-dioxa-cyclopenta[a]cyclopropa[e]cyclodecen-7-one 
• 70868-30-3 (1aR,4R,5S,5aS,8S,8aS,10aR)-5-Hydroxy-4,8,10a-trimethyl-decahydro-1,6-dioxa-cyclopenta[a]cyclopropa[e]cyclodecen-7-one 
• 105882-28-8 C₂₄H₄₄O₂Si 
• 70868-29-0 (1aR,4R,5aS,8S,8aS,10aR)-4,8,10a-Trimethyl-octahydro-1,6-dioxa-cyclopenta[a]cyclopropa[e]cyclodecene-5,7-dione 
• 105882-29-9 (S)-2-((E)-(1R,4R,7S,10R)-1,7-Dimethyl-11-oxa-bicyclo[8.1.0]undec-5-en-4-yl)-propionic acid methyl ester 
• 10171-89-8 (S)-2-((2E,7E)-(1R,4S)-4,8-Dimethyl-cyclodeca-2,7-dienyl)-propionic acid methyl ester 
• 10171-88-7 (S)-2-((2E,7E)-(1R,4S)-4,8-Dimethyl-cyclodeca-2,7-dienyl)-propionic acid 
• 61228-90-8 Methanesulfonic acid (E)-(3S,3aS,10R,11R,11aS)-3,6,10-trimethyl-2-oxo-2,3,3a,4,5,8,9,10,11,11a-decahydro-cyclodeca[b]furan-11-yl ester 
• 553-21-9 costunolide 

Downstream Products

• 23527-07-3 saussurea lactone 
• 32223-12-4 11β,13-dihydroreynosin 
• 22387-64-0 dihydro-β-cyclocostunolide 
• 10180-76-4 (3S,3aS,5aR,9aR,9bS)-3,5a,9-Trimethyl-3a,4,5,5a,6,7,9a,9b-octahydro-3H-naphtho[1,2-b]furan-2-one 

Relevant academic research and scientific papers

Synthesis of (+)-8-deoxyvernolepin and its 11,13-dihydroderivative. A novel reaction initiated by sulfene elimination leads to the 2-oxa-cis-decalin skeleton

The title compounds are interesting candidates for antifungal screening. This paper describes the enantiospecific synthesis of these compounds starting from (+)-costunolide isolated from a commercially available extract. We used two novel reactions as key synthetic steps in this work: the acid-induced cyclization of an δ,ε-epoxy ester, which stereoselectively gave a hydroxymethyl-substituted δ-lactone, with the hydroxyalkyl group in the desired β-equatorial disposition, and a reaction cascade, initiated by a base-promoted sulfene elimination, which led to a 10-oxiranyl-2-oxa-cis-decalin from the mesylate of a trans-fused δ-lactone. We also found that the reaction between selenium dioxide and the 1,5-diene system of elemanolides gave selenadecalins analogous to natural eudesmanolides. Our results prove that the synthetic strategy employed, on the basis of biomimetic concepts, is a useful procedure for the enantiospecific preparation of (+)-vernolepin-related compounds from accessible germacrolides.

STIMULATION OF WITCHWEED GERMINATION BY SESQUITERPENE LACTONES: A STRUCTURE-ACTIVITY STUDY

Twenty-four natural and synthetic sesquiterpene lactones were tested as witchweed germination stimulants to determine the essential structural requirements for the stimulation of witchweed germination by dihydroparthenolide.All of the 10 germacranolides tested induced 40-65 percent germination of witchweed across a broad concentration range, from 10-5 to 10-9 M.The highest activity was observed with a mixture of the two eudesmanolides, santamarin and reynosin.These findings indicate that it is the spatial arrangement of the germacrane-eudesmane skeleton in conjunction with the five-membered lactone ring which is important in the promotion of witchweed germination, rather than the presence of any specific functional group on the molecule.The structure of these compounds is similar to portions of the active molecule (+)-strigol.

Total Synthesis of (+)-Dihydrocostunolide via Tandem Cope-Claisen Rearrangement

The total synthesis of (+)-dihydrocostunolide via tandem Cope-Claisen rearrangement has been accomplished.

Ti-catalyzed transannular cyclization of epoxygermacrolides. Synthesis of antifungal (+)-tuberiferine and (+)-dehydrobrachylaenolide

We present a divergent strategy for the stereoselective synthesis of both eudesmanolides (+)-tuberiferine and (+)-brachylaenolide starting from the accessible germacrolide (+)-costunolide. The key steps of these syntheses are the Ti-catalyzed transannular cyclization of a 1,4-epoxygermacrolide in the presence or absence of water, respectively. The catalytic cycle operating in the presence of water probably involves the reduction of a tertiary radical by H-atom transfer from aquacomplex Cp2TiIII(OH2)Cl. The catalytic cycle under anhydrous conditions presumably occurs through mixed disproportionation between a tertiary radical and Cp2TiIIICl. Synthetic (+)-tuberiferine and (+)-brachylaenolide displayed an antifungal potency against Phycomyces blakesleeanus comparable or even higher than amphotericin B, the gold standard for antifungal therapy.

Sesquiterpene lactones with potential use as natural herbicide models (I): trans, trans-germacranolides

A structure-activity study to evaluate the effect of the trans,trans- germacranolide sesquiterpene lactones costunolide, parthenolide, and their 1,10-epoxy and 11,13-dihydro derivatives (in a range of 100-0.001 μM) on the growth and germination of several mono and dicotyledon target species is accomplished. Results are compared with those obtained in the same bioassay with an internal standard, the commercial herbicide Logran, to validate the results with a known active formulation and to compare the results with a commercial product to test their potential use as natural herbicide models. These compounds appear to have a more selective effects on the radicle growth of monocotyledons. Certain factors such as the presence of nucleophile- acceptor groups and their accessibility enhance the inhibitory activity. The levels of radicle inhibition obtained with some compounds on wheat are totally comparable to those of Logran and allow to propose them as lead compounds.

A new strategy for the synthesis of (+)-vernolepin related compounds: An unusual sulfene elimination leads to the 2-oxa-cis-decalin skeleton

A new strategy for the synthesis of (+)-vernolepin (1), (+)-vernodalin (2), and (+)-8-deoxyvernolepin (3), from the accessible germacrolides (+)-salonitenolide (4) and (+)-costunolide (5), has been developed. The key steps in the synthesis are a Cope rearrangement from the germacradiene to the elemadiene skeleton, the cyclization of a trans-fused δ-lactone from an epoxy ester, and an unusual sulfene elimination, which promotes a reaction cascade leading to the 2-oxa-cis-decalin skeleton. (C) 2000 Elsevier Science Ltd.

Microbial transformation of sesquiterpene lactones by the fungi Cunninghamella echinulata and Rhizopus oryzae

Incubations of the fungi Cunninghamella echinulata and Rhizopus oryzae with the sesquiterpene lactones (+)-costunolide (1), (+)-cnicin (2), (+)- salonitenolide (3), (-)-dehydrocostuslactone (4), (-)-lychnopholide (5), and (-)-eremantholide C (6) were performed. Incubation of 1 with C. echinulata afforded Δ(11(13))-dihydrogenation and Δ(1(10))-epoxidation products (7- 10). C. echinulata also hydrolyzed the side chain of 2, and transformed 4 into (+)-11α,13-dihydrodehydrocostuslactone (12), a new natural product. R. oryzae converted 4 into both Δ(11(13))-dihydrogenation and Δ(10(14))- epoxidation products (16 and 17). Both fungi transformed 5 into (-)-16-(1- methyl-1-propenyl)eremantholanolide (13), providing experimental evidence for the biosynthesis of the eremantholide hemiketal unit. Compounds 3 and 6 were not metabolized by either fungus under the test conditions.