200859-98-9

Upstream product

• 200859-96-7 (1S,3R,4S)-3-(methoxymethoxy)-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-2-one 
• 200859-97-8 (1S,2S,3R,4S)-2-((Z)-2-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-vinyl)-3-methoxymethoxy-7,7-dimethyl-1-((Z)-2-phenylsulfanyl-vinyl)-bicyclo[2.2.1]heptan-2-ol 
• 74-88-4 methyl iodide 

Downstream Products

• 200860-04-4 Trifluoro-acetic acid (Z)-(1R,4S,5S,6S,7R,8S)-4-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-7-methoxymethoxy-5,11,11-trimethyl-6-(2,2,2-trifluoro-acetoxy)-bicyclo[6.2.1]undec-2-en-1-yl ester 
• 200860-09-9 (1S,2S,4S,5S,6R,8R,9S)-1,6-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-8-methoxymethoxy-6,12,12-trimethyl-3-oxa-tricyclo[7.2.1.0^2,4]dodecan-7-one 
• 200860-07-7 (Z)-(1S,2R,4R,5S,8R)-4,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one 
• 200860-06-6 (Z)-(1S,2R,4S,5S,8R)-8-Hydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one 
• 200860-00-0 (5E,7E)-(1S,2R,4S)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undeca-5,7-dien-3-one 
• 200860-05-5 (Z)-(1R,4S,5S,6S,7R,8S)-4-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-7-methoxymethoxy-5,11,11-trimethyl-bicyclo[6.2.1]undec-2-ene-1,6-diol 
• 200860-11-3 (Z)-(1S,2R,4S,5S,8R)-2,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one 
• 200860-12-4 (1S,2S,4S,5R,6S,8R,9S)-1,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-6,12,12-trimethyl-3-oxa-tricyclo[7.2.1.0^2,4]dodecan-7-one 
• 200860-02-2 (E)-(1S,2R,3S,4S,5S,6R)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-6-phenylsulfanyl-bicyclo[6.2.1]undec-7-en-3-ol 
• 200859-94-5 (E)-(1S,2R,3R,4S,5S,6R)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-6-phenylsulfanyl-bicyclo[6.2.1]undec-7-en-3-ol 
• 200859-99-0 (E)-(1S,2R,4S,5S,6R)-6-Benzenesulfinyl-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undec-7-en-3-one 

Relevant academic research and scientific papers

Application of an S → O Allylic Transposition in the Context of a Bridgehead Olefinic System. New Opportunities for the Structural Modification of Bicyclo[6.2.1]undecanes via Transannular Ring Closure

A practical route is described for the preparation of allylic sulfide 8, whose double bond resides at a bridgehead site. Following hydride reduction of the ketone carbonyl and sulfoxidation, exposure to trifluoroacetic anhydride results in the operation of an intermolecular S → O allylic transposition. This central step leads to 14a, an intermediate useful for probing the consequences associated with epoxidation of its cis-cyclononene double bond. A total of three different transannular cyclizations are described in order to demonstrate the ease with which ring closures can operate in a medium-ring setting of this type. Represented are transformations that generate tetrahydrofuran, oxetane, and cyclopropane subunits. The kinetic biases favoring these transformations are highlighted.