60426-81-5

Upstream product

• 60403-31-8 (3aS,4aR,5R,7aR,8S,9aR)-5-tert-Butoxy-4a,8-dimethyl-3-methylene-decahydro-azuleno[6,5-b]furan-2-one 
• 72341-86-7 3aα,4,4a,5,6,7,7aα,8,9,9aα-decahydro-5β-hydroxy-4aβ,8β-dimethylazuleno<6,5-b>furan-2(3)H-one 
• 123130-59-6 3-(1-methylethenyl)-2-<2-<(trimethylsilyl)methyl>allyl>-2-cyclopenten-1-one 
• 114506-14-8 (<1SR,3aSR,4SR,7SR,8aSR>-1-(t-Butyldimethylsiloxy)-4,8a-dimethyloctahydro-6(1H)-azulenon-7-yl)essigsaeure ethylester 
• 114506-15-9 [(3S,3aS,5S,8S,8aS)-3-(tert-Butyl-dimethyl-silanyloxy)-3a,8-dimethyl-6-oxo-decahydro-azulen-5-yl]-acetic acid 
• 72341-88-9 (3aS,4aR,5R,7aR,8R,9aS)-5-Hydroxy-4a,8-dimethyl-2-oxo-dodecahydro-azuleno[6,5-b]furan-3-carboxylic acid 
• 105787-84-6 3-(<1SR,2SR,5SR>-2-(t-Butyldimethylsiloxy)-5-isopropenyl-1-methylcyclopentyl)propionitril 
• 105787-85-7 3-(<1SR,2SR,5SR>-2-(t-Butyldimethylsiloxy)-5-isopropenyl-1-methylcyclopentyl)propionaldehyd 
• 105787-87-9 <1SR,3aSR,6SR,8aSR>-1-(t-Butyldimethylsiloxy)-8a-methyl-4-methylen-decahydro-6-azulenol 
• 105787-86-8 <1SR,6RS,8aSR>-1-(t-Butyldimethylsiloxy)-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-6-azulenol 
• 105787-86-8 <1SR,6SR,8aSR>-1-(t-Butyldimethylsiloxy)-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-6-azulenol 
• 105787-83-5 3-((1S,5S)-2-Hydroxy-5-isopropenyl-1-methyl-cyclopentyl)-propionitrile 
• 114506-13-7 (1S,3aS,4S,6S,8aS)-1-(tert-Butyl-dimethyl-silanyloxy)-4,8a-dimethyl-decahydro-azulen-6-ol 
• 105787-88-0 <1SR,8aSR>-1-(t-Butyldimethylsiloxy)-4,8a-dimethyl-1,2,3,7,8,8a-hexahydro-6(5H)-azulenon 

Downstream Products

• 5945-42-6 (+/-)-aromaticin 

Relevant academic research and scientific papers

Allylsilane-Based Annulations. Direct Stereoselective Syntheses of (+/-)-Graveolide and (+/-)-Aromaticin

An allylsilane-based annulation was used to construct a functionalized perhydroazulene.The C(1), C(5), and C(10) stereocenters, characteristic of the helenanolides, were established using a reductive alkylation strategy.Stereoselective syntheses of the pseudoguaianolides graveolide and aromaticin were achieved.

Total Synthesis of the Pseudoguaianolide (+)-Confertin

The first total synthesis of the pseudoguaianolide (+)-confertin (1) begins with the preparation of the enantiomerically pure cyclopropane derivative 6b and its stereospecific ring expansion furnishing the five-membered ring A-building block 8a.The AB ketone 21d is produced by intermolecular Michael addition, Lewis acid catalyzed intramolecular hetero-ene reaction, and a pair of oxidation/reduction reactions.Fusion of the heterocyclic five-membered ring and α-methylenation of the ABC intermediate 35c is accomplished by well-known technology.The structure of essential synthetic intermediates has been determined by 2D-NMR, CD spectroscopy, or single crystal X-ray analysis.The whole synthesis starts from α-chloroacetone and reaches the target compound 1 after 22 steps.

An Annulation Approach to the Synthesis of Pseudoguaianolide Sequiterpene Lactones. Total Syntheses of dl-Confertin and dl-Aromatin

Annulation of 2-methyl-1,3-cyclopentanedione with 4-(halomethyl)-5-(1-oxopropyl)-3-furancarboxylic esters 6a or 6b provides the fully assembled tricyclic framework, 1, of the cytotoxic pseudoguaianolide sequiterpene lactones.Dienedione 1 has been used to construct (+/-)-confertin (2) and (+/-)-aromatin (3).Experiments relevant to a total synthesis of the more complex helenanolides (e.g., the fastigilins, 4) also are discussed.