59633-89-5

Upstream product

• 59633-88-4 2-(bromomethyl)-1,3,3-trimethylcyclohex-1-ene 
• 105-45-3 acetoacetic acid methyl ester 
• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 
• 616-38-6 carbonic acid dimethyl ester 
• 118672-99-4 3-oxo-5-(2,6,6-trimethyl-cyclohex-2-enyl)-pentanoic acid methyl ester 
• 79-77-6 (E)-β-ionone 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 472-20-8 β-cyclogeraniol 

Downstream Products

• 152294-12-7 3-[2-(2,6,6-Trimethyl-cyclohex-1-enyl)-ethyl]-4H-isoxazol-5-one 
• 59633-93-1 Toluene-4-sulfonic acid (1S,4aS,8aS)-5,5,8a-trimethyl-2-oxo-decahydro-naphthalen-1-ylmethyl ester 
• 59633-92-0 1-<<(p-tolylsulfonyl)oxy>methyl>-2-hydroxy-5,5,8a-trimethyldecahydronaphthalene 
• 59633-91-9 8ξ-hydroxy-9β-hydroxymethyl-(4α,4β),10β-trimethyl-(trans)-decahydronaphthalene 
• 95998-96-2 ((6aS,11aR)-4,4,9,11a-Tetramethyl-1,2,3,4,5,6,7,10,11,11a-decahydro-cyclohepta[a]naphthalen-6a-yl)-methanol 
• 59633-91-9 8β-hydroxy-9β-hydroxymethyl-(4α,4β),10β-trimethyl-(trans)-decahydronaphthalene 
• 59633-91-9 rac-12-nor-drimane-8α,11-diol 
• 3738-00-9 (±)-ambrox 
• 10207-83-7 (+/-)-(1α,2β,4aβ,8aα)-decahydro-2-hydroxyl-2,5,5,8a-tetramethyl-1-naphthaleneethanol 
• 16892-20-9 rac-5,5,8a-Trimethyldecal-2-one 
• 293312-51-3 (11R,S)-11-(2',5'-di(tetrahydropyran-2-yloxy)-1'-phenyl)drim-7-en-11-ol 
• 293310-05-1 C₃₁H₄₆O₄ 
• 39707-59-0 isozonarone 
• 39707-55-6 (+)-isozonarol 

Relevant academic research and scientific papers

110. The Synthesis of Racemic Ambrox

(+/-)-Ambrox (10), the racemic form of (-)-Ambrox, the commercially most important ambergris odorant has been synthesized from a readily available bicyclic keto ester in five steps.The racemic ether retains the characteristic scent of fine-quality ambergris, and the odor threshold of the racemate and the (-)-enantiomer prepared from natural sclareol found to be essentially identical.

Preparation of 9α-fluorinated sesquiterpenic drimanes and evaluation of their antifeedant activities

The preparation of 9α-fluoro analogues of both natural and unnatural drimane-type sesquiterpenes is described. Their synthesis began with the initial preparation of methyl 8-keto-12-nordriman-11-oate from β-ionone and entailed the electrophilic fluorination of C-9 for the stereoselective introduction of the fluorine atom. The drimane skeleton was completed from, the intermediate 9α-fluoro-8-keto-12-nordrimane system by means of different reactions at the C-8 ketone carbonyl group, essentially Wittig methylenation, cyanohydrin formation or palladium-catalysed carbonylation of the corresponding enol triflate. Further manipulation of the functionalization derived from these key reactions allowed the preparation, among others, of 9α-fluorodrimanes, which are structurally and functionally related to albicanic acid, drimenin and olepupuane. Also described are the reactivities of some of the fluorine-containing systems prepared and a comparative study of the antifeedant activities of a selection of 9α-fluorodrimanes and the corresponding hydrogen analogues against several, insect species with different feeding ecologies (Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi), which revealed a significant increase in the antifeedant activities of some of the fluorinated drimane analogues.

Studies toward synthesis of bioactive labdanes: Efficient synthesis of 9β-carbomethoxy-4 α, 4β, 10β-trimethyl-(trans)- decahydronaphthalen-8-one

Methyl-5-(2′,6′,6′-trimethylcyclohex-2′-enyl) -3-ketopentanoate 10 has been successfully cyclised to 9β-carbomethoxy- 4α,4β,10β-trimethyl-(trans)-decahydro-naphthalen-8-one 1. Out of the different reaction conditions used, stannic chloride in moist dichlo

Total synthesis of yahazunol, zonarone and isozonarone

The synthesis of the marine natural products zonarone and isozonarone was achieved via (+)-albicanic acid, a sesquiterpene of the drimane type. Coupling of the appropiate drimane-synthon with lithiated hydroquinone ethers led to sesquiterpene arenes, which were further modified to the target molecules. Stereoselective epoxidation followed by regioselective opening of the oxirane ring yielded yahazunol.

Beta-ketoester compounds

The beta-ketoesters of formula I are useful as precursors for organoleptic compounds, especially for flavors, fragrances and masking agents and antimicrobial compounds.

A conjugate addition-radical cyclisation approach to sesquiterpene-phenol natural products

A conjugate addition-radical cyclization approach to sesquiterpenephenol natural products was discussed. The first step involved the conjugate addition of an organocopper species to a chromone-3-carboxylate which resulted in 2,2-disubstituted chroman-4-ones. The second step was the generation of a β-ketoester radical. The last step involved a stereoselective manganese(III) acetate-mediated radical cyclization reaction.

Common synthetic strategy for optically active cyclic terpenoids having a 1,1,5-trimethyl-trans-decalin nucleus: Syntheses of (+)-acuminolide, (-)-spongianolide A, and (+)-scalarenedial

We have developed a simple and practical method for providing enantiomerically pure bi-, tri-, and tetracyclic frameworks having a 1,1,5-trimethyl-trans-decalin nucleus, and demonstrated their utility for terpenoid synthesis. Thus, we achieved the stereocontrolled total syntheses of (+)-acuminolide as a bicyclic, (-)-spongianolide A as a tricyclic, and (+)-scalarenedial as a tetracyclic terpenoid from the corresponding optically pure cyclic β-ketoesters, which were obtained by repeating the same method of the ring construction, including the olefin cyclization with Lewis acid, followed by simple optical resolution using chiral auxiliaries for acetal formation, respectively. This is a general and valuable strategy for the synthesis of enantiomerically pure cyclic terpenoids having the 1,1,5-trimethyl-trans-decalin nucleus.

Beta-ketoester compounds

The beta-ketoesters of formula I are useful as precursors for organoleptic compounds, especially for flavors, fragrances and masking agents and antimicrobial compounds.

Total synthesis of the marine sesquiterpene hydroquinones zonarol and isozonarol and the sesquiterpene quinones zonarone and isozonarone

The total synthesis of the naturally occurring sesquiterpene hydroquinones zonarol and isozonarol and the sesquiterpene quinones zonarone and isozonarone was achieved starting from β-ionone, which was transformed via (+)-albicanic acid to (+)-albicanal and (-)-drim-7-en-11-al. Coupling of the aldehydes with lithiated hydroquinone ethers and further modification of the coupling products led to the target molecules. (C) 2000 Elsevier Science Ltd.

STUDIES TOWARD THE TOTAL SYNTHESIS OF POLYOXYGENATED LABDANES: PRELIMINARY APPROACHES

Using the keto-ester 3 as a starting material, methods are developed for the successive introduction of hydroxy groups at C-6, C-7 and C-8 of a decalin system, as well as for elaboration of a C-9 pentadiene chain in preliminary approach to the total synthesis of trihydroxylabdadienes.