The Experts below are selected from a list of 633 Experts worldwide ranked by ideXlab platform
Chunchen Liao - One of the best experts on this subject based on the ideXlab platform.
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Dual behavior of masked o-benzoquinones in intramolecular Diels-Alder reactions. Expedient synthesis of highly functionalized cis-decalins from 2-methoxyphenols.
Journal of Organic Chemistry, 2005Co-Authors: Rama Krishna Peddinti, Santhosh Kumar Chittimalla, Chunchen LiaoAbstract:The potential dual behavior as dienes and dienophiles of the diene moieties of masked o-benzoquinones (MOBs) 10a−e−12a−e, generated upon oxidation of 2-methoxyphenols 1−3 with BTIB in the presence of appropriate dienols, in their intramolecular Diels−Alder (IMDA) reactions has been examined. The IMDA reactions of MOBs 10a−d, 11a,b,d, and 12a,b,d resulted in highly functionalized oxatricyclic compounds 18a−d, 19a,b,d, and 20a,b,d, respectively, with concomitant formation of cis-decalin derivatives 21a−d, 22a,b,d, and 23a,b,d in a highly regio- and stereoselective manner. However, the MOBs 10e−12e provided exclusively oxatricyclic compounds 18e−20e. The formation of cis-decalins in these IMDA reactions illustrates the dienophilic character of MOBs, in addition to their behavior as dienes. The ratio of the two cycloadducts obtained in each reaction as a result of the dual character of MOBs depends on the nature and/or position of the substituents on both the cyclohexadienone moiety and the added 2,4-dienol. ...
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dual behavior of masked o benzoquinones in intermolecular diels alder reactions with acyclic dienes a rapid entry to polyfunctionalized bicyclo 2 2 2 oct 5 en 2 ones and cis decalins
Journal of Organic Chemistry, 2004Co-Authors: Chienhsing Chen, Rama Krishna Peddinti, N Kameswara S Rao, Chunchen LiaoAbstract:The potentiality of the masked o-benzoquinones, i.e., 6,6-dimethoxy-2,4-cyclohexadienones 5−8, to react both as dienes and dienophiles in their intermolecular reactions has been demonstrated. The masked o-benzoquinones (MOBs) 5−8 generated in situ from 2-methoxyphenols 1−4 underwent intermolecular Diels−Alder cycloadditions with acyclic 1,3-dienes 9a−e to provide bicyclo[2.2.2]octenones 10a−f−13a−f along with cis-decalin derivatives 14a−f−17a−f with regio- and stereoselectivity, except in the case of MOB 8. The formation of cis-decalins in these Diels−Alder reactions illustrates the dienophilic character of MOBs, in addition to their general behavior as dienes. The ratio of the two cycloadducts obtained in each reaction as a result of the dual character of MOBs depends on the nature and/or position of the substituents on both the cyclohexadienone moiety and the added conjugated acyclic diene. All of the cycloadducts resulted from the diene property of MOBs in intermolecular Diels−Alder reactions smoothly ...
Masahisa Nakada - One of the best experts on this subject based on the ideXlab platform.
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synthetic studies on bucidarasin c two diastereoselective transannular reactions producing cis Decaline derivatives that show reversal selectivity
Tetrahedron Letters, 2012Co-Authors: Akinobu Nakahara, Misaki Kanbe, Masahisa NakadaAbstract:Abstract This manuscript describes studies on the construction of the cis -Decaline core of (+)-bucidarasin C. The transannular Diels–Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis -Decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis -Decaline derivative as the major product.
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Synthetic studies on (+)-bucidarasin C: Two diastereoselective transannular reactions producing cis-Decaline derivatives that show reversal selectivity
Tetrahedron Letters, 2012Co-Authors: Akinobu Nakahara, Misaki Kanbe, Masahisa NakadaAbstract:Abstract This manuscript describes studies on the construction of the cis -Decaline core of (+)-bucidarasin C. The transannular Diels–Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis -Decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis -Decaline derivative as the major product.
Akinobu Nakahara - One of the best experts on this subject based on the ideXlab platform.
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synthetic studies on bucidarasin c two diastereoselective transannular reactions producing cis Decaline derivatives that show reversal selectivity
Tetrahedron Letters, 2012Co-Authors: Akinobu Nakahara, Misaki Kanbe, Masahisa NakadaAbstract:Abstract This manuscript describes studies on the construction of the cis -Decaline core of (+)-bucidarasin C. The transannular Diels–Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis -Decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis -Decaline derivative as the major product.
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Synthetic studies on (+)-bucidarasin C: Two diastereoselective transannular reactions producing cis-Decaline derivatives that show reversal selectivity
Tetrahedron Letters, 2012Co-Authors: Akinobu Nakahara, Misaki Kanbe, Masahisa NakadaAbstract:Abstract This manuscript describes studies on the construction of the cis -Decaline core of (+)-bucidarasin C. The transannular Diels–Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis -Decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis -Decaline derivative as the major product.
Rama Krishna Peddinti - One of the best experts on this subject based on the ideXlab platform.
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Dual behavior of masked o-benzoquinones in intramolecular Diels-Alder reactions. Expedient synthesis of highly functionalized cis-decalins from 2-methoxyphenols.
Journal of Organic Chemistry, 2005Co-Authors: Rama Krishna Peddinti, Santhosh Kumar Chittimalla, Chunchen LiaoAbstract:The potential dual behavior as dienes and dienophiles of the diene moieties of masked o-benzoquinones (MOBs) 10a−e−12a−e, generated upon oxidation of 2-methoxyphenols 1−3 with BTIB in the presence of appropriate dienols, in their intramolecular Diels−Alder (IMDA) reactions has been examined. The IMDA reactions of MOBs 10a−d, 11a,b,d, and 12a,b,d resulted in highly functionalized oxatricyclic compounds 18a−d, 19a,b,d, and 20a,b,d, respectively, with concomitant formation of cis-decalin derivatives 21a−d, 22a,b,d, and 23a,b,d in a highly regio- and stereoselective manner. However, the MOBs 10e−12e provided exclusively oxatricyclic compounds 18e−20e. The formation of cis-decalins in these IMDA reactions illustrates the dienophilic character of MOBs, in addition to their behavior as dienes. The ratio of the two cycloadducts obtained in each reaction as a result of the dual character of MOBs depends on the nature and/or position of the substituents on both the cyclohexadienone moiety and the added 2,4-dienol. ...
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dual behavior of masked o benzoquinones in intermolecular diels alder reactions with acyclic dienes a rapid entry to polyfunctionalized bicyclo 2 2 2 oct 5 en 2 ones and cis decalins
Journal of Organic Chemistry, 2004Co-Authors: Chienhsing Chen, Rama Krishna Peddinti, N Kameswara S Rao, Chunchen LiaoAbstract:The potentiality of the masked o-benzoquinones, i.e., 6,6-dimethoxy-2,4-cyclohexadienones 5−8, to react both as dienes and dienophiles in their intermolecular reactions has been demonstrated. The masked o-benzoquinones (MOBs) 5−8 generated in situ from 2-methoxyphenols 1−4 underwent intermolecular Diels−Alder cycloadditions with acyclic 1,3-dienes 9a−e to provide bicyclo[2.2.2]octenones 10a−f−13a−f along with cis-decalin derivatives 14a−f−17a−f with regio- and stereoselectivity, except in the case of MOB 8. The formation of cis-decalins in these Diels−Alder reactions illustrates the dienophilic character of MOBs, in addition to their general behavior as dienes. The ratio of the two cycloadducts obtained in each reaction as a result of the dual character of MOBs depends on the nature and/or position of the substituents on both the cyclohexadienone moiety and the added conjugated acyclic diene. All of the cycloadducts resulted from the diene property of MOBs in intermolecular Diels−Alder reactions smoothly ...
Misaki Kanbe - One of the best experts on this subject based on the ideXlab platform.
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synthetic studies on bucidarasin c two diastereoselective transannular reactions producing cis Decaline derivatives that show reversal selectivity
Tetrahedron Letters, 2012Co-Authors: Akinobu Nakahara, Misaki Kanbe, Masahisa NakadaAbstract:Abstract This manuscript describes studies on the construction of the cis -Decaline core of (+)-bucidarasin C. The transannular Diels–Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis -Decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis -Decaline derivative as the major product.
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Synthetic studies on (+)-bucidarasin C: Two diastereoselective transannular reactions producing cis-Decaline derivatives that show reversal selectivity
Tetrahedron Letters, 2012Co-Authors: Akinobu Nakahara, Misaki Kanbe, Masahisa NakadaAbstract:Abstract This manuscript describes studies on the construction of the cis -Decaline core of (+)-bucidarasin C. The transannular Diels–Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis -Decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis -Decaline derivative as the major product.
