62075-35-8

Upstream product

• 114300-64-0 4-methyl-4-vinylcyclohex-2-enone 
• 38614-36-7 2-methylpropen-1-ylmagnesium bromide 
• 113105-07-0 (7R,8R)-7-Dimethylcarbamoyl-8-methyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid 
• 66088-37-7 ethyl 1-methyl-2-oxocyclohexancarboxylate 
• 6561-08-6 1-Methyl-1-vinyl-cyclohex-2-en 
• 147254-14-6 cyclohexanol, 4-ethenyl-4-methyl-3-(1-methylethenyl)- 
• 49768-04-9 1-Methyl-cyclohexen-⁽²⁾-carbonsaeure-aethylester 
• 110144-12-2 (8R,9S)-8-Isopropenyl-9-methyl-1,5-dithia-spiro[5.5]undecane-9-carboxylic acid ethyl ester 
• 110144-07-5 (E)-4-[2-(2-Hydroxy-ethyl)-[1,3]dithian-2-yl]-2-methyl-but-2-enoic acid methyl ester 
• 110144-14-4 (8R,9S)-8-Isopropenyl-9-methyl-1,5-dithia-spiro[5.5]undecane-9-carbaldehyde 
• 110144-13-3 ((8R,9S)-8-Isopropenyl-9-methyl-1,5-dithia-spiro[5.5]undec-9-yl)-methanol 
• 74320-47-1 (1S,2S,5S)-2-Methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester 
• 113105-12-7 C₁₆H₂₅NO₇ 
• 74320-51-7 (7R,8R)-7-Dimethylcarbamoyl-8-methyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid methyl ester 

Downstream Products

• 73211-80-0 (1S,2S)-4-Dibromomethylene-2-isopropenyl-1-methyl-1-vinyl-cyclohexane 

Relevant academic research and scientific papers

Construction of the 1,2-dialkenylcyclohexane framework via ireland-claisen rearrangement and intramolecular barbier reaction: Application to the synthesis of ()-geijerone and a diastereoisomeric mixture with its 5-epimer

The elemene-type terpenoids, which possess various biological activities, contain a syn- or anti-1,2-dialkenylcyclohexane framework. An efficient synthetic route to the syn- and anti-1,2-dialkenylcyclohexane core and its application in the synthesis of ()-geijerone and its diastereomer is reported. Construction of the syn- and anti-1,2-dialkenyl moiety was achieved via Ireland-Claisen rearrangement of the (E)-Allylic ester, and the cyclohexanone moiety was derived from the iodoaldehyde via intramolecular Barbier reaction. The synthetic strategy allows rapid access to various epimers and analogues of elemene-type products.

STEREOSELECTIVE ALKYLATION OF ESTER LACTONE. SYNTHESIS OF-GEIJERONE AND FORMAL SYNTHESIS OF dl-γ-ELEMENE

Geijerone 1 was synthesized in racemic form via stereoselective alkylation of an ester lactone conformationally fixed with its bridged lactone ring. dl-γ-Elemene 2 has already been obtained from 1.

Stereoselective Construction of Functionalized cis-1,2-Dialkylcyclohexanecarboxylates: A Novel Synthesis of (+/-)-Geijerone and γ-Elemene

General applicability of our intramolecular ester enolate alkylation method to the stereoselective construction of functionalized cis-1,2-dialkylcyclohexanecarboxylates is illustrated in the context of a novel synthesis of (+/-)-geijerone and a formal syn