Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin
Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (∼$50 USD/kg) i...
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| Published in | Journal of the American Chemical Society Vol. 138; no. 51; pp. 16616 - 16619 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
28.12.2016
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (∼$50 USD/kg) in 12 steps using extensive site-selective C(sp3)–H bond functionalization. Significantly, this work represents a novel oxidative strategic template for future approaches to these natural products and their analogs. |
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| AbstractList | Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (∼$50 USD/kg) in 12 steps using extensive site-selective C(sp³)–H bond functionalization. Significantly, this work represents a novel oxidative strategic template for future approaches to these natural products and their analogs. Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (~$50 USD/kg) in 12-steps using extensive site-selective C(sp 3 )–H bond functionalization. Significantly, this work represents a novel oxidative strategic template for future approaches to these natural products and their analogs. Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (∼$50 USD/kg) in 12 steps using extensive site-selective C(sp )-H bond functionalization. Significantly, this work represents a novel oxidative strategic template for future approaches to these natural products and their analogs. Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (∼$50 USD/kg) in 12 steps using extensive site-selective C(sp3)-H bond functionalization. Significantly, this work represents a novel oxidative strategic template for future approaches to these natural products and their analogs.Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (∼$50 USD/kg) in 12 steps using extensive site-selective C(sp3)-H bond functionalization. Significantly, this work represents a novel oxidative strategic template for future approaches to these natural products and their analogs. Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (∼$50 USD/kg) in 12 steps using extensive site-selective C(sp3)–H bond functionalization. Significantly, this work represents a novel oxidative strategic template for future approaches to these natural products and their analogs. Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (similar to$50 USD/kg) in 12 steps using extensive site-selective C(sp(3))-H bond functionalization. Significantly, this work represents a novel oxidative strategic template for future approaches to these natural products and their analogs. |
| Author | Maimone, Thomas J Morikawa, Takahiro Condakes, Matthew L Hung, Kevin |
| AuthorAffiliation | Department of Chemistry |
| AuthorAffiliation_xml | – name: Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Kevin surname: Hung fullname: Hung, Kevin – sequence: 2 givenname: Matthew L surname: Condakes fullname: Condakes, Matthew L – sequence: 3 givenname: Takahiro surname: Morikawa fullname: Morikawa, Takahiro – sequence: 4 givenname: Thomas J orcidid: 0000-0001-5823-692X surname: Maimone fullname: Maimone, Thomas J email: maimone@berkeley.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27966918$$D View this record in MEDLINE/PubMed |
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| Keywords | ALCOHOLS JIADIFENOLIDE NATURAL-PRODUCTS (+/-)-MERRILACTONE-A NEUROTROPHIC ACTIVITY C-H OXIDATION (-)-JIADIFENOLIDE ENANTIOSELECTIVE TOTAL-SYNTHESIS SECO-PREZIZAANE DIRECTED DIHYDROXYLATION |
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| Snippet | Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant... Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant... |
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| SubjectTerms | bioactive properties cedrol Chemistry Chemistry, Multidisciplinary feedstocks Illicium Physical Sciences Science & Technology synthesis |
| Title | Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin |
| URI | http://dx.doi.org/10.1021/jacs.6b11739 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000391081800013 https://www.ncbi.nlm.nih.gov/pubmed/27966918 https://www.proquest.com/docview/1852674376 https://www.proquest.com/docview/2000368995 https://pubmed.ncbi.nlm.nih.gov/PMC5261859 |
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