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Exploring an Alternative Synthetic Pathway for the Total Synthesis of (±)-Nordasycarpidol and (±)-Nordasycarpidone
A total synthesis of the strychnos alkaloids, dasycarpidol and nordasycarpidone, has been accomplished from 2-(3-ethyl-1-oxo-2,3,4,9-tetrahydro-1 H -carbazol-2-yl)acetonitrile 1 , which is the C-2 ethyl side chain of carbazole as well as carbazole-fused lactone 3 that is conveniently of the key azoc...
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| Published in: | Chemistry of natural compounds 2023-07, Vol.59 (4), p.715-720 |
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| Main Authors: | , |
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| Language: | English |
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| container_end_page | 720 |
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| container_title | Chemistry of natural compounds |
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| creator | Uludag, Nesimi Nevarsa, Alev Orhan |
| description | A total synthesis of the strychnos alkaloids, dasycarpidol and nordasycarpidone, has been accomplished from 2-(3-ethyl-1-oxo-2,3,4,9-tetrahydro-1
H
-carbazol-2-yl)acetonitrile
1
, which is the C-2 ethyl side chain of carbazole as well as carbazole-fused lactone
3
that is conveniently of the key azocino[4,3-b]indole skeleton
6
. These syntheses of the target natural products are accomplished without a protecting group, which has a carbonyl group at the C-1 position of the carbazole. These alternative routes are accomplished by shortening the number of steps with high efficiency and also nordasycarpidol
8
synthesized for the first time in the literature. The structures of all the presently synthesized compounds were confirmed using spectroscopic methods (FT-IR,
1
H NMR,
13
C NMR). |
| doi_str_mv | 10.1007/s10600-023-04095-4 |
| format | article |
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H
-carbazol-2-yl)acetonitrile
1
, which is the C-2 ethyl side chain of carbazole as well as carbazole-fused lactone
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that is conveniently of the key azocino[4,3-b]indole skeleton
6
. These syntheses of the target natural products are accomplished without a protecting group, which has a carbonyl group at the C-1 position of the carbazole. These alternative routes are accomplished by shortening the number of steps with high efficiency and also nordasycarpidol
8
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1
H NMR,
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H
-carbazol-2-yl)acetonitrile
1
, which is the C-2 ethyl side chain of carbazole as well as carbazole-fused lactone
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that is conveniently of the key azocino[4,3-b]indole skeleton
6
. These syntheses of the target natural products are accomplished without a protecting group, which has a carbonyl group at the C-1 position of the carbazole. These alternative routes are accomplished by shortening the number of steps with high efficiency and also nordasycarpidol
8
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1
H NMR,
13
C NMR).</description><subject>Acetonitrile</subject><subject>alkaloids</subject><subject>Carbazoles</subject><subject>Carbonyl groups</subject><subject>Carbonyls</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>indoles</subject><subject>Natural products</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic Chemistry</subject><subject>Plant Sciences</subject><subject>spectroscopy</subject><subject>Strychnos</subject><subject>Synthesis</subject><issn>0009-3130</issn><issn>1573-8388</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kc1KAzEUhYMoWKsv4CrgRhfRm95MJrMU8Q-KCuo6pGliR8bJmKRqH8tX8MmcWkEQcXW5937nLM4hZJfDIQcojxIHCcBghAwEVAUTa2TAixKZQqXWyQAAKoYcYZNspfTYr0pKNSD59K1rQqzbB2paetxkF1uT6xdHbxdtnrlcW3pj8uzVLKgPkfYneheyab7_qU40eLr_8X7ArkKcmrSwJnb1NDS94fSvR-u2yYY3TXI733NI7s9O704u2Pj6_PLkeMwsAmaGFqzkbgpYGu6c5EaVlZ1YAOm98SX3rqz4BCfWF6isEY57lGgkF35ksMAh2V_5djE8z13K-qlO1jWNaV2YJ419VkIWolqie7_QxzDvo2iSHilRqkIUVdVToxVlY0gpOq-7WD-ZuNAc9LIIvSpC90XoryK06EW4EqVumbOLP9b_qD4BqleNiw</recordid><startdate>20230701</startdate><enddate>20230701</enddate><creator>Uludag, Nesimi</creator><creator>Nevarsa, Alev Orhan</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7S9</scope><scope>L.6</scope></search><sort><creationdate>20230701</creationdate><title>Exploring an Alternative Synthetic Pathway for the Total Synthesis of (±)-Nordasycarpidol and (±)-Nordasycarpidone</title><author>Uludag, Nesimi ; Nevarsa, Alev Orhan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c303t-3c0c61ed037a1ee61a879cbc006ffaf71fe791b3bcf538ca4e1f363a614f2a353</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acetonitrile</topic><topic>alkaloids</topic><topic>Carbazoles</topic><topic>Carbonyl groups</topic><topic>Carbonyls</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>indoles</topic><topic>Natural products</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic Chemistry</topic><topic>Plant Sciences</topic><topic>spectroscopy</topic><topic>Strychnos</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Uludag, Nesimi</creatorcontrib><creatorcontrib>Nevarsa, Alev Orhan</creatorcontrib><collection>CrossRef</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Chemistry of natural compounds</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Uludag, Nesimi</au><au>Nevarsa, Alev Orhan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Exploring an Alternative Synthetic Pathway for the Total Synthesis of (±)-Nordasycarpidol and (±)-Nordasycarpidone</atitle><jtitle>Chemistry of natural compounds</jtitle><stitle>Chem Nat Compd</stitle><date>2023-07-01</date><risdate>2023</risdate><volume>59</volume><issue>4</issue><spage>715</spage><epage>720</epage><pages>715-720</pages><issn>0009-3130</issn><eissn>1573-8388</eissn><abstract>A total synthesis of the strychnos alkaloids, dasycarpidol and nordasycarpidone, has been accomplished from 2-(3-ethyl-1-oxo-2,3,4,9-tetrahydro-1
H
-carbazol-2-yl)acetonitrile
1
, which is the C-2 ethyl side chain of carbazole as well as carbazole-fused lactone
3
that is conveniently of the key azocino[4,3-b]indole skeleton
6
. These syntheses of the target natural products are accomplished without a protecting group, which has a carbonyl group at the C-1 position of the carbazole. These alternative routes are accomplished by shortening the number of steps with high efficiency and also nordasycarpidol
8
synthesized for the first time in the literature. The structures of all the presently synthesized compounds were confirmed using spectroscopic methods (FT-IR,
1
H NMR,
13
C NMR).</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10600-023-04095-4</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-3130 |
| ispartof | Chemistry of natural compounds, 2023-07, Vol.59 (4), p.715-720 |
| issn | 0009-3130 1573-8388 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_3040465495 |
| source | Springer Nature |
| subjects | Acetonitrile alkaloids Carbazoles Carbonyl groups Carbonyls Chemistry Chemistry and Materials Science Chemistry/Food Science indoles Natural products NMR Nuclear magnetic resonance Organic Chemistry Plant Sciences spectroscopy Strychnos Synthesis |
| title | Exploring an Alternative Synthetic Pathway for the Total Synthesis of (±)-Nordasycarpidol and (±)-Nordasycarpidone |
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