108944-92-9

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 108944-91-8 (1R,4aS,8aS)-(-)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene 
• 59633-90-8 (4aS,8aS)-3,4,4aα,5,6,7,8,8aβ-octahydro-5,5,8aβ-trimethyl-1-methylidene-2(1H)-naphthalenone 
• 108888-66-0 (1R,2S,4aS,8aS)-5,5,8a-Trimethyl-2-((R)-1-naphthalen-1-yl-ethylcarbamoyloxy)-decahydro-naphthalene-1-carboxylic acid methyl ester 
• 59633-92-0 (1S,2S,4aS,8aS)-(+)-1-(p-tosyloxy)methyl-2-hydroxy-5,5,8a-trimethyldecahydronaphthalene 
• 59633-93-1 (1S,4aS,8aS)-(-)-1-(p-tosyloxy)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene 
• 3796-70-1 trans geranyl acetone 
• 54632-04-1 (±)-albicanol 
• 150-78-7 1,4-dimethoxybezene 
• 426239-07-8 10,11-epoxyfarnesyl bromide 
• 28444-34-0 10,11-epoxyfarnesol 
• 16776-04-8 (1β,4aα,8aβ)-decahydro-5,5,8a-trimethyl-1-naphthalenol 
• 52782-49-7 (+/-)-5β-hydroxy-1,1,4aβ-trimethyl-1,4,4a,5,6,7,8,8aα-octahydronaphthalen-2(3H)-one 
• 63598-65-2 (+/-)-5,5,8a-trimethyl-1-methylen-(4ar,8at)-octahydro-naphthalen-2-one 

Downstream Products

• 39707-54-5 (+/-)-zonarol 
• 39707-56-7 (+)-zonarone 
• 39707-54-5 (-)-ent-zonarol 

Relevant academic research and scientific papers

A concise route for the synthesis of tetracyclic meroterpenoids: (±)-aureol preparation and mechanistic interpretation

A new concise general methodology for the synthesis of different tetracyclic meroterpenoids is reported: (±)-aureol (1), the key intermediate of this general route. The synthesis of (±)-aureol (1) was achieved in seven steps (28% overall yield) from (±)-a

Synthesis of (±)-aureol by bioinspired rearrangements

A bioinspired and sustainable procedure for the straightforward synthesis of (±)-aureol has been achieved in eight steps (14% overall yield) from epoxyfarnesol. The key steps are the titanocene(III)-catalyzed radical cascade cyclization of an epoxyfarneso

Transition-metal-catalyzed allylic substitution and titanocene-catalyzed epoxypolyene cyclization as a powerful tool for the preparation of terpenoids

Many biologically active substances are composed of sesquiterpene units linked to aromatic structures, especially substituted phenols. Here, we describe an efficient synthetic approach to this class of natural product from commercially available substances in a short sequence. The key transformations involve allylic substitution reactions using a palladium or copper catalyst and titanocene-catalyzed epoxypolyene cyclization reactions via radicals. The polycyclic core structures are accessed with high chemo- and stereocontrol. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.