41410-55-3

Upstream product

• 1193-18-6 3-methylcyclohexen-2-one 
• 5090-50-6 (3S,3aS,5aR,6R,9S,9aS,9bS)-6,9-Dihydroxy-3,5a,9-trimethyl-decahydro-naphtho[1,2-b]furan-2-one 
• 5090-75-5 4β-hydroxy-1-oxo-5αH,6,11βH-eudesman-6,13-olide 
• 83037-75-6 2-(1,2,3,4,4a,5,6,7,8,8aα-decahydro-1α-hydroxy-4aβ-methyl-5,8-dioxo-naphtalen-2β-yl)propionic acid methyl ester 
• 83037-74-5 2-((1R,6S,8S)-1-Methyl-7-oxo-2,5-bis-trimethylsilanyloxy-tricyclo[4.4.0.0^2,5]dec-8-yl)-propionic acid methyl ester 
• 95709-90-3 1β-t.butyldimethylsilyloxy-4β-hydroxy-5αH,6,11βH-eudesman-6,12-olide 
• 95682-54-5 (1S,4R,4aR,6aS,7S,11aS,11bS)-4-(tert-Butyl-dimethyl-silanyloxy)-1,4a,7,10,10-pentamethyl-dodecahydro-9,11-dioxa-cyclohepta[a]naphthalen-1-ol 
• 95682-52-3 2S-(1,2,3,4,4a,5,6,7,8,8aα-decahydro-5β-hydroxy-4aβ-methyl-1α-trimethylsilyloxy-8-oxo-naphtalen-2β-yl)-propanol 
• 95682-53-4 (4R,4aR,6aS,7S,11aS,11bS)-4-Hydroxy-4a,7,10,10-tetramethyl-decahydro-9,11-dioxa-cyclohepta[a]naphthalen-1-one 
• 95682-55-6 2S-(1,2,3,4,4a,5,6,7,8,8aα-decahydro-5β-t.butyldimethylsilyloxy-1α,8β-dihydroxy-4aβ,8α-dimethyl-naphtalen-2β-yl)-propanol 
• 95682-50-1 (1S,4R,4aR,6aS,7S,11aS,11bS)-1,4a,7,10,10-Pentamethyl-dodecahydro-9,11-dioxa-cyclohepta[a]naphthalene-1,4-diol 
• 95682-51-2 2S-(1,2,3,4,4a,5,6,7,8,8aα-decahydro-1α,5β,8β-trihydroxy-4aβ,8α-dimethyl-naphtalen-2β-yl)-propanol 
• 83037-78-9 (R)-2-((1R,2R,4aS,8aR)-4a-Methyl-5,8-dioxo-1-trimethylsilanyloxy-decahydro-naphthalen-2-yl)-propionic acid methyl ester 
• 83037-73-4 6-(1'-methylcarbonyl-ethyl)-3-methyl-2-cyclohexenone 

Downstream Products

• 99267-88-6 Toluene-4-sulfonic acid (3S,3aS,5aS,6R,9aR,9bS)-9a-hydroxy-3,5a-dimethyl-9-methylene-2-oxo-dodecahydro-naphtho[1,2-b]furan-6-yl ester 
• 99267-87-5 C₂₂H₂₈O₆S 
• 99297-03-7 Toluene-4-sulfonic acid (3S,3aS,5aR,6R,9bS)-3,5a,9-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester 
• 23522-05-6 1-keto-6β,7α,11β-H-selin-4(5)-en-6,12-olide 

Relevant academic research and scientific papers

Effects of solvents and water in Ti(III)-mediated radical cyclizations of epoxygermacrolides. Straightforward synthesis and absolute stereochemistry of (+)-3α-hydroxyreynosin and related eudesmanolides

The Cp2TiCl-mediated rearrangement of 1,10-epoxy-11β,13-dihydrocostunolide (4) was carried out using different solvents and additives to develop an expeditious procedure for the synthesis of natural eudesmanolides via free-radical chemistry. In the nonhalogenated solvents THF, benzene, and toluene the transannular cyclization, initiated by the homolytic opening of the oxirane ring, selectively led to the desired exocyclic alkene 5. When water was added to THF, however, the main product was reduced eudesmanolide 8. Experiments with D2O confirmed that the H-4 of 8 comes from water. To rationalize these results, a mechanistic hypothesis based on a water-solvated Cp2TiCl complex is proposed. Finally, the usefulness of Cp2TiCl for the synthesis of natural eudesmanolides has been proved using this reagent in the key step for the chemical preparation of (+)-3α-hydroxyreynosin (1) and (+)-reynosin (17). These syntheses confirmed the chemical structure of 1 and established the absolute stereochemistry of the natural products 1 and 17. The results obtained suggest that the combination of the biomimetic strategy employed, with Ti(III)-mediated free-radical chemistry, may come to represent a general method for the enantiospecific synthesis of more than 170 natural eudesmanolides containing an exocyclic double bond between C-4 and C-15.

TERPENOIDS OF Artemisia splendens

d-Camphor, l-borneol, stearic acid, β-sitosterol, austricin, and a new sesquiterpene lactone which has been called splendolide have been isolated from the epigeal part of Artemisia splendens Willd.The structure of splendolide has been established as 1β-hydroxy-6βH,7αH-eudesma-4,11(13)-dien-6,12-olide.

THE TOTAL SYNTHESIS OF 1-OXYGENATED EUDESMANOLIDES

A route towards 1-oxygenated eudesmanolides, via a (2+2) photocycloaddition reaction for constructing the decalin framework is described.The following natural substances have been synthesized. (+/-)-dihydroreynosin (1), (+/-)-1-oxo-dihydromagnolialide (2)