68365-89-9

Upstream product

• 138152-06-4 (3Z,7E)-4,8,12-Trimethyltrideca-3,7,11-trien-1-ol 
• 459-89-2 (3E,7E)-homofarnesol 
• 110202-08-9 (Z)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol 
• 110202-07-8 (E)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol 
• 564-20-5 trans-syn-cis norambreinolide 
• 99733-97-8 3-methyl-5-(2',6',6'-trimethylcyclohex-1'-enyl)-1-penten-3-ol 
• 127-41-3 alpha-ionone 
• 22850-55-1 (E)-6,10-dimethyl-5,9-undecadien-1-yne 
• 105014-28-6 (4aR,8aS)-1-Allyl-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol 
• 10207-83-7 (1S,2R,8aS)-1-(2-Hydroxy-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol 
• 320756-17-0 biscyclohomofarnesane-8α,12-diol 
• 3738-00-9 Isoambrox 
• 10207-83-7 (8α-Methyl)-iresan-8β,11-diol 
• 35826-67-6 homofarnesol 

Downstream Products

• 3738-00-9 (3aRS,5aSR,9aRS,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan 
• 3738-00-9 (-)-norlabdane 
• 122566-19-2 <3aR-(3aα,4α,6aα,10aS^*)> dodecahydro-3a,4,7,7-tetramethyl-2H-naphtho<8a,1-b>furan 

Relevant academic research and scientific papers

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.

Synthesis and Applications of Cyclohexenyl Halides Obtained by a Cationic Carbocyclisation Reaction

The synthesis of cyclic alkenyl halides (mainly fluorides, chlorides and bromides) from alkynol or enyne derivatives by an acid-mediated cationic cyclisation reaction is disclosed. This high-yielding, scalable and technically simple method complements and challenges conventional methodologies. This study includes the development of biomimetic cationic cyclisation reactions of polyenyne derivatives to give interesting halogen-containing polycyclic compounds. The application of this reaction in the key step of the synthesis of two terpenes, namely austrodoral and pallescensin A, and the potent odorant 9-epi-Ambrox demonstrates the potential of the reaction for natural product synthesis.

Diastereoselective Synthesis of (±)-Ambrox by Titanium(III)-Catalyzed Radical Tandem Cyclization

A synthesis of (±)-ambrox, a compound with delicious ambergris-type scent, is presented. The key step is a highly diastereoselective titanocene(III)-catalyzed radical tandem cyclization of a farnesol derivative.

Scalable Synthesis of the Amber Odorant 9-epi-Ambrox through a Biomimetic Cationic Cyclization/Nucleophilic Bromination Reaction

A novel biomimetic nucleophilic bromocyclization reaction is used in the key step of a new and straightforward synthesis of 9-epi-Ambrox, an organic compound of high interest and value in the context of fragrances. This strategic reaction allows access to 9-epi-Ambrox on a gram scale from a dienyne derivative, easily available from geraniol, following a sequence of seven steps (35% global yield) with just one purification process. Both enantiomers of the molecule were obtained by a challenging enzymatic resolution.

(3E, 7E)- homo- farnesol improved production method

The present invention relates to novel processes for improved preparation of homofarnesol, especially of (3E,7E)-homofarnesol and homofarnesol preparations having an elevated content of (3E,7E)-homofarnesol (also referred to as all-E-homofarnesol).

Synthesis of five-membered cyclic ethers by reaction of 1,4-diols with dimethyl carbonate

The reaction of 1,4-diols with dimethyl carbonate in the presence of a base led to selective and high-yielding syntheses of related five-membered cyclic ethers. This synthetic pathway has the potential for a wide range of applications. Distinctive cyclic ethers and industrially relevant compounds were synthesized in quantitative yield. The reaction mechanism for the cyclization was investigated. Notably, the chirality of the starting material was maintained. DFT calculations indicated that the formation of five-membered cyclic ethers was energetically the most favorable pathway. Typically, the selectivity exhibited by these systems could be rationalized on the basis of hard-soft acid-base theory. Such principles were applicable as far as computed energy barriers were concerned, but in practice cyclization reactions were shown to be entropically driven. Copyright

Trans-tetrahydrofurans by OH-assisted Ru-catalyzed isomerization of 2-butene-1,4-diols

We herein report a general method for the synthesis of 1,2-annulated trans-tetrahydrofurans by the OH-assisted Ru-catalyzed isomerization of (Z)-2-butene-1,4-diols (using Chaudret's catalyst), followed by reduction of the incipient lactol (using Et3SiH and Amberlyst 15). Alternatively, the lactol can be oxidized to the corresponding lactone (using Ikariya's catalyst). It was shown by labeling experiments that an addition/elimination pathway is (at least to some extent) operative for the isomerization reaction. Only 0.5 mol-% of Chaudret's Ru catalyst is sufficient for the rapid and stereoselective isomerization of enediols of the type shown. This allows ready access to trans-tetrahydrofurans.

Internal nucleophilic termination in acid-mediated polyene cyclizations part 3. Synthetic access to didehydro and methyl didehydro analogues of (±)-ambrox

Treatment of the unsaturated allenic alcohols (E)-7, (Z)-7, 10, 13, and 19 with an excess of FSO3H in 2-nitropropane at -90° to -30° afforded, in 68-85% yield, diastereoisomer mixtures of racemic tricyclic ethers 14a-d and 20a-d, respectively (Schemes 3 and 5), with high stereoselectivity (see Table and Scheme 6). These stereospecific transformations represent the first reported examples of an acid-mediated polyene cyclization, in which an alkene is the initiating group and an allenic alcohol serves as the internal terminator. In close analogy to our earlier work, a nonsynchronous process is postulated, whereby the stereochemical course of cyclization is directed by the conformational structure of an intermediate cyclohexyl cation (see Schemes 3 and 6). In addition, the organoleptic properties of 14c and 20c, racemic didehydro and methyl didehydro analogues, respectively, of the known odorant Ambrox ((-)-4f), are briefly discussed.

Conversion of Esters and Lactones to Ethers via Thionoesters and Thionolactones Using Reductive Radical Desulfurization

Various thionoesters and thionolactones are readily reduced into the corresponding ethers in high isolated yields by radical desulfuurization with organotin hydrides and Et3B under mild reaction conditions.

Synthesis of d,l-Norlabdane Oxide and Related Odorants: An Intramolecular Radical Approach

A cascade radical approach to d,l-norlabdane oxide and related odorants is reported. Oxidative radical cyclization of polyene 4 with Mn(III) and Cu(II) afforded exclusively bicycle 3, which upon acid treatment gave tricycle 2 possessing the norlabdane oxide skeleton with a modified A-ring system. Tricycle 2 was ultimately converted to d, l-norlabdane oxide 1 and to several new A-ring labdane oxides as potential odorants.