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Synthesis of methyl dihydrohardwickiate and its C-4 epimer.: Structural amendment of natural crolechinic acid
Reduction of the α,β-unsaturated ester moiety of (+)-methyl hardwickiate with magnesium in methanol afforded methyl (4a S,6 S,8a S,1 R,5 R)-5,6,8a-trimethyl-5-[2′-(3″-oxoyl)-ethyl-perhydro-1-naphthalenyl]-carboxaylate, while reduction with sodium in n-propanol, followed by esterification with diazom...
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| Published in: | Phytochemistry (Oxford) 2000-04, Vol.53 (8), p.851-854 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| container_end_page | 854 |
| container_issue | 8 |
| container_start_page | 851 |
| container_title | Phytochemistry (Oxford) |
| container_volume | 53 |
| creator | Costa, Marta Perles, Elaine C. Fujiwara, Fred Y. Imamura, Paulo M. |
| description | Reduction of the α,β-unsaturated ester moiety of (+)-methyl hardwickiate with magnesium in methanol afforded methyl (4a
S,6
S,8a
S,1
R,5
R)-5,6,8a-trimethyl-5-[2′-(3″-oxoyl)-ethyl-perhydro-1-naphthalenyl]-carboxaylate, while reduction with sodium in
n-propanol, followed by esterification with diazomethane, furnished its C-4 epimer. After comparison of the
1
H
- and
13
C
-NMR data of these compounds with those reported for crolechinic acid isolated from
Croton lechleri, a stereochemical revision for the natural product is suggested. |
| doi_str_mv | 10.1016/S0031-9422(99)00583-X |
| format | article |
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S,6
S,8a
S,1
R,5
R)-5,6,8a-trimethyl-5-[2′-(3″-oxoyl)-ethyl-perhydro-1-naphthalenyl]-carboxaylate, while reduction with sodium in
n-propanol, followed by esterification with diazomethane, furnished its C-4 epimer. After comparison of the
1
H
- and
13
C
-NMR data of these compounds with those reported for crolechinic acid isolated from
Croton lechleri, a stereochemical revision for the natural product is suggested.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/S0031-9422(99)00583-X</identifier><identifier>PMID: 10820791</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>(+)-Methyl hardwickiate ; Biological and medical sciences ; Chemical constitution ; Crolechinic acid ; Diterpenes - chemical synthesis ; Diterpenes - chemistry ; Fundamental and applied biological sciences. Psychology ; Magnesium - chemistry ; Magnetic Resonance Spectroscopy ; Plant physiology and development ; Reduction ; Stereochemistry ; Stereoisomerism</subject><ispartof>Phytochemistry (Oxford), 2000-04, Vol.53 (8), p.851-854</ispartof><rights>2000 Elsevier Science Ltd</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1341083$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10820791$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Costa, Marta</creatorcontrib><creatorcontrib>Perles, Elaine C.</creatorcontrib><creatorcontrib>Fujiwara, Fred Y.</creatorcontrib><creatorcontrib>Imamura, Paulo M.</creatorcontrib><title>Synthesis of methyl dihydrohardwickiate and its C-4 epimer.: Structural amendment of natural crolechinic acid</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Reduction of the α,β-unsaturated ester moiety of (+)-methyl hardwickiate with magnesium in methanol afforded methyl (4a
S,6
S,8a
S,1
R,5
R)-5,6,8a-trimethyl-5-[2′-(3″-oxoyl)-ethyl-perhydro-1-naphthalenyl]-carboxaylate, while reduction with sodium in
n-propanol, followed by esterification with diazomethane, furnished its C-4 epimer. After comparison of the
1
H
- and
13
C
-NMR data of these compounds with those reported for crolechinic acid isolated from
Croton lechleri, a stereochemical revision for the natural product is suggested.</description><subject>(+)-Methyl hardwickiate</subject><subject>Biological and medical sciences</subject><subject>Chemical constitution</subject><subject>Crolechinic acid</subject><subject>Diterpenes - chemical synthesis</subject><subject>Diterpenes - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Magnesium - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Plant physiology and development</subject><subject>Reduction</subject><subject>Stereochemistry</subject><subject>Stereoisomerism</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><recordid>eNpF0cuKFDEUBuAgitMz-ghKFiK6qDGXqkriRqQZLzDgohVmF1Inp6hoXdokpfTbm55udRESDh8_5PyEPOPsmjPevtkxJnllaiFeGfOasUbL6u4B2XCtZCUVYw_J5h-5IJcpfWdFNW37mFxwpgVThm_ItDvMecAUEl16OmEeDiP1YTj4uAwu-t8BfgSXkbrZ05AT3VY1xX2YMF6_pbscV8hrdCN1E86-nHzMmd1pCHEZEYYwB6AOgn9CHvVuTPj0fF-Rbx9uvm4_VbdfPn7evr-tUBiRK3BadKLmYJiTPSimeNv1bYcKGl53Ruuu0Q1Aq5nvnenqpuflKXWt6jLs5RV5ecrdx-XniinbKSTAcXQzLmuyinOppBAFPj_DtZvQ230Mk4sH-3dBBbw4A5fAjX10M4T038m6UFnYuxPD8qtfAaNNEHAG9CEiZOuXUDLtsTl735w91mKNsffN2Tv5BzYGiq8</recordid><startdate>20000401</startdate><enddate>20000401</enddate><creator>Costa, Marta</creator><creator>Perles, Elaine C.</creator><creator>Fujiwara, Fred Y.</creator><creator>Imamura, Paulo M.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20000401</creationdate><title>Synthesis of methyl dihydrohardwickiate and its C-4 epimer.: Structural amendment of natural crolechinic acid</title><author>Costa, Marta ; Perles, Elaine C. ; Fujiwara, Fred Y. ; Imamura, Paulo M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-e292t-ca82b241c90a3fc70716bf6be7c514b988b585cc680dfa9b45f180d38474c68f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>(+)-Methyl hardwickiate</topic><topic>Biological and medical sciences</topic><topic>Chemical constitution</topic><topic>Crolechinic acid</topic><topic>Diterpenes - chemical synthesis</topic><topic>Diterpenes - chemistry</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Magnesium - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Plant physiology and development</topic><topic>Reduction</topic><topic>Stereochemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Costa, Marta</creatorcontrib><creatorcontrib>Perles, Elaine C.</creatorcontrib><creatorcontrib>Fujiwara, Fred Y.</creatorcontrib><creatorcontrib>Imamura, Paulo M.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Costa, Marta</au><au>Perles, Elaine C.</au><au>Fujiwara, Fred Y.</au><au>Imamura, Paulo M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of methyl dihydrohardwickiate and its C-4 epimer.: Structural amendment of natural crolechinic acid</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2000-04-01</date><risdate>2000</risdate><volume>53</volume><issue>8</issue><spage>851</spage><epage>854</epage><pages>851-854</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>Reduction of the α,β-unsaturated ester moiety of (+)-methyl hardwickiate with magnesium in methanol afforded methyl (4a
S,6
S,8a
S,1
R,5
R)-5,6,8a-trimethyl-5-[2′-(3″-oxoyl)-ethyl-perhydro-1-naphthalenyl]-carboxaylate, while reduction with sodium in
n-propanol, followed by esterification with diazomethane, furnished its C-4 epimer. After comparison of the
1
H
- and
13
C
-NMR data of these compounds with those reported for crolechinic acid isolated from
Croton lechleri, a stereochemical revision for the natural product is suggested.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>10820791</pmid><doi>10.1016/S0031-9422(99)00583-X</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0031-9422 |
| ispartof | Phytochemistry (Oxford), 2000-04, Vol.53 (8), p.851-854 |
| issn | 0031-9422 1873-3700 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_71137322 |
| source | Elsevier:Jisc Collections:Elsevier Read and Publish Agreement 2022-2024:Freedom Collection (Reading list) |
| subjects | (+)-Methyl hardwickiate Biological and medical sciences Chemical constitution Crolechinic acid Diterpenes - chemical synthesis Diterpenes - chemistry Fundamental and applied biological sciences. Psychology Magnesium - chemistry Magnetic Resonance Spectroscopy Plant physiology and development Reduction Stereochemistry Stereoisomerism |
| title | Synthesis of methyl dihydrohardwickiate and its C-4 epimer.: Structural amendment of natural crolechinic acid |
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