Construction of Iterative Tetrahydrofuran Ring Units and Total Synthesis of (+)-Goniocin
Cytotoxic acetogenin (+)-goniocin has been synthesized in 17 steps from (R)-O-tritylglycidol. The core structure of the contiguous C22–C10 threo-trans-threo-trans-threo-trans-tris-tetrahydrofuran (THF) ring involving an iterative THF-ring unit was synthesized. An iterative THF ring unit was construc...
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| Published in | Organic letters Vol. 18; no. 9; pp. 2248 - 2251 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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American Chemical Society
06.05.2016
Amer Chemical Soc |
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| Abstract | Cytotoxic acetogenin (+)-goniocin has been synthesized in 17 steps from (R)-O-tritylglycidol. The core structure of the contiguous C22–C10 threo-trans-threo-trans-threo-trans-tris-tetrahydrofuran (THF) ring involving an iterative THF-ring unit was synthesized. An iterative THF ring unit was constructed from an alkenyl-substituted THF ring in four steps including a Pd(II)-catalyzed ring-closing reaction and cross-metathesis. This method is general and allows the preparation of both trans-threo-trans- and trans-threo-cis-THF ring units flexibly. |
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| AbstractList | Cytotoxic acetogenin (+)-goniocin has been synthesized in 17 steps from (R)-O-tritylglycidol. The core structure of the contiguous C22-C10 threo-trans-threo-trans-threo-trans-tris-tetrahydrofuran (THF) ring involving an iterative THF-ring unit was synthesized. An iterative THF ring unit was constructed from an alkenyl-substituted THF ring in four steps including a Pd(II)-catalyzed ring-closing reaction and cross-metathesis. This method is general and allows the preparation of both trans-threo-trans- and trans-threo-cis-THF ring units flexibly. Cytotoxic acetogenin (+)-goniocin has been synthesized in 17 steps from (R)-O-tritylglycidol. The core structure of the contiguous C-22-C-10 threo-trans-threo-trans-threo-trans-tris-tetrahydrofuran (THF) ring involving an iterative THF-ring unit was synthesized. An iterative THF ring unit was constructed from an alkenyl-substituted THF ring in four steps including a Pd(II)-catalyzed ring-closing reaction and cross-metathesis. This method is general and allows the preparation of both trans-threo-trans- and trans-threo-cis-THF ring units flexibly. Cytotoxic acetogenin (+)-goniocin has been synthesized in 17 steps from (R)-O-tritylglycidol. The core structure of the contiguous C22–C10 threo-trans-threo-trans-threo-trans-tris-tetrahydrofuran (THF) ring involving an iterative THF-ring unit was synthesized. An iterative THF ring unit was constructed from an alkenyl-substituted THF ring in four steps including a Pd(II)-catalyzed ring-closing reaction and cross-metathesis. This method is general and allows the preparation of both trans-threo-trans- and trans-threo-cis-THF ring units flexibly. |
| Author | Nakagishi, Tetsuya Sasaki, Mai Ueda, Tsuyoshi Hoshiya, Naoyuki Uenishi, Jun’ichi Suzuki, Ai |
| AuthorAffiliation | Kyoto Pharmaceutical University |
| AuthorAffiliation_xml | – name: Kyoto Pharmaceutical University |
| Author_xml | – sequence: 1 givenname: Ai surname: Suzuki fullname: Suzuki, Ai – sequence: 2 givenname: Mai surname: Sasaki fullname: Sasaki, Mai – sequence: 3 givenname: Tetsuya surname: Nakagishi fullname: Nakagishi, Tetsuya – sequence: 4 givenname: Tsuyoshi surname: Ueda fullname: Ueda, Tsuyoshi – sequence: 5 givenname: Naoyuki surname: Hoshiya fullname: Hoshiya, Naoyuki – sequence: 6 givenname: Jun’ichi surname: Uenishi fullname: Uenishi, Jun’ichi email: juenishi@mb.kyoto-phu.ac.jp |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27111729$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1021_acs_joc_6b02432 crossref_primary_10_1016_j_ccr_2017_09_003 crossref_primary_10_1038_s41570_018_0115 crossref_primary_10_1039_D1QO01049B crossref_primary_10_1002_chem_201803064 crossref_primary_10_1002_anie_201710482 crossref_primary_10_1055_a_2058_0355 crossref_primary_10_1021_jacs_3c01985 crossref_primary_10_1021_acs_chemrev_9b00414 crossref_primary_10_1021_acs_orglett_8b02706 crossref_primary_10_1002_ange_201710482 crossref_primary_10_1021_acs_orglett_7b01161 |
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| Keywords | GONIOTHALAMUS-GIGANTEUS THF (6S,7S,9R,10R)-6,9-EPOXYNONADEC-18-ENE-7,10-DIOL OXIDATIVE POLYCYCLIZATIONS ORGANOMETALLIC REAGENTS EFFICIENT SYNTHESIS STEREOSELECTIVE-SYNTHESIS ANNONACEOUS ACETOGENINS ASYMMETRIC TOTAL-SYNTHESIS BROWN ALGA |
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| Snippet | Cytotoxic acetogenin (+)-goniocin has been synthesized in 17 steps from (R)-O-tritylglycidol. The core structure of the contiguous C22–C10... Cytotoxic acetogenin (+)-goniocin has been synthesized in 17 steps from (R)-O-tritylglycidol. The core structure of the contiguous C-22-C-10... Cytotoxic acetogenin (+)-goniocin has been synthesized in 17 steps from (R)-O-tritylglycidol. The core structure of the contiguous C22-C10... |
| Source | Web of Science |
| SourceID | proquest crossref pubmed webofscience acs |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 2248 |
| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Construction of Iterative Tetrahydrofuran Ring Units and Total Synthesis of (+)-Goniocin |
| URI | http://dx.doi.org/10.1021/acs.orglett.6b00877 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000375891700077 https://www.ncbi.nlm.nih.gov/pubmed/27111729 https://search.proquest.com/docview/1787480028 |
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