Synthesis of 3-(Glycosyloxymethyl)isocoumarins and (S)-3-(Glycosyloxymethyl)-3,4-dihydroisocoumarins by Coupling of Propargyl Glycosides with 2-Iodobenzoic Acid Mediated by Palladium Complex and Zinc Chloride
ABSTRACT Palladium-catalyzed coupling of propargyl glycosides with O-iodobenzoic acid leads to the selective syntheses of hitherto unknown, novel isocoumarin glycosides in 43-55% yields. We have observed that reduction of the keto acids to the corresponding alcohols was highly stereospecific due to...
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| Veröffentlicht in: | Synthesis (Stuttgart) 2006-09, Vol.2006 (17), p.2944-2950 |
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| container_issue | 17 |
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| container_title | Synthesis (Stuttgart) |
| container_volume | 2006 |
| creator | Mereyala, Hari Babu Pathuri, Gopal |
| description | ABSTRACT
Palladium-catalyzed coupling of propargyl glycosides with O-iodobenzoic acid leads to the selective syntheses of hitherto unknown, novel isocoumarin glycosides in 43-55% yields. We have observed that reduction of the keto acids to the corresponding alcohols was highly stereospecific due to the neighboring glycosyl substitution and leads to the formation of (S)-3-(glycosyloxymethyl)-3,4-dihydroisocoumarins in 21-37% overall yield. |
| doi_str_mv | 10.1055/s-2006-942504 |
| format | Article |
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Palladium-catalyzed coupling of propargyl glycosides with O-iodobenzoic acid leads to the selective syntheses of hitherto unknown, novel isocoumarin glycosides in 43-55% yields. We have observed that reduction of the keto acids to the corresponding alcohols was highly stereospecific due to the neighboring glycosyl substitution and leads to the formation of (S)-3-(glycosyloxymethyl)-3,4-dihydroisocoumarins in 21-37% overall yield.</description><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNp1kbtOwzAUhi0EEqUwsntsJQxO7NzGquJSqYhKBQmxRI7tNK6cuLJTgXknXoJH4IlIaJcOTGf5zncuPwCXAb4OcBTdOBRiHKOMhhGmR2AQUJKgMMCvx2CAMclQkqbBKThzbo0xTkKSDcDP0jdtJZ1y0JSQoNG99tw4r82Hr2VbeT1WznCzrZlVjYOsEXC0HKND8vtrzyJyRZFQlRfWHPQVHk7NdqNVs-oHLazZMLvyGu4sSkgH31VbwRDNjDCFbD6N4nDClYCPUijWStFLFkxrJtS27nT1RsuPv43eVMPhtNLGdqJzcFIy7eTFvg7By93t8_QBzZ_uZ9PJHPEwoS0q4oTgIilpXPAiEpSFWRBh0r0oZjShIuOFTBllskw5LiiLk54hKYswE2EUkyFAOy-3xjkry3xjVXeuzwOc94HkLu8DyXeBdPzVjm8rJWuZr83WNt2C_-C_Q7ORXA</recordid><startdate>20060901</startdate><enddate>20060901</enddate><creator>Mereyala, Hari Babu</creator><creator>Pathuri, Gopal</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20060901</creationdate><title>Synthesis of 3-(Glycosyloxymethyl)isocoumarins and (S)-3-(Glycosyloxymethyl)-3,4-dihydroisocoumarins by Coupling of Propargyl Glycosides with 2-Iodobenzoic Acid Mediated by Palladium Complex and Zinc Chloride</title><author>Mereyala, Hari Babu ; Pathuri, Gopal</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c274t-b6730b7f46bcb5d4a2915038816a474d9cbe8a4aef8c0b4a67d4a238a50ad2563</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mereyala, Hari Babu</creatorcontrib><creatorcontrib>Pathuri, Gopal</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mereyala, Hari Babu</au><au>Pathuri, Gopal</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 3-(Glycosyloxymethyl)isocoumarins and (S)-3-(Glycosyloxymethyl)-3,4-dihydroisocoumarins by Coupling of Propargyl Glycosides with 2-Iodobenzoic Acid Mediated by Palladium Complex and Zinc Chloride</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2006-09-01</date><risdate>2006</risdate><volume>2006</volume><issue>17</issue><spage>2944</spage><epage>2950</epage><pages>2944-2950</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>ABSTRACT
Palladium-catalyzed coupling of propargyl glycosides with O-iodobenzoic acid leads to the selective syntheses of hitherto unknown, novel isocoumarin glycosides in 43-55% yields. We have observed that reduction of the keto acids to the corresponding alcohols was highly stereospecific due to the neighboring glycosyl substitution and leads to the formation of (S)-3-(glycosyloxymethyl)-3,4-dihydroisocoumarins in 21-37% overall yield.</abstract><doi>10.1055/s-2006-942504</doi><tpages>7</tpages></addata></record> |
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| ispartof | Synthesis (Stuttgart), 2006-09, Vol.2006 (17), p.2944-2950 |
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| source | Thieme Connect Journals |
| title | Synthesis of 3-(Glycosyloxymethyl)isocoumarins and (S)-3-(Glycosyloxymethyl)-3,4-dihydroisocoumarins by Coupling of Propargyl Glycosides with 2-Iodobenzoic Acid Mediated by Palladium Complex and Zinc Chloride |
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