A Concise Total Synthesis of (−)‐Berkelic Acid
Reported here is a concise total synthesis of (−)‐berkelic acid in eight linear steps. This synthesis features a Catellani reaction/oxa‐Michael cascade for the construction of the isochroman scaffold, a one‐pot deprotection/spiroacetalization operation for the formation of the tetracyclic core struc...
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| Published in | Angewandte Chemie International Edition Vol. 60; no. 10; pp. 5141 - 5146 |
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| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
01.03.2021
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
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| Abstract | Reported here is a concise total synthesis of (−)‐berkelic acid in eight linear steps. This synthesis features a Catellani reaction/oxa‐Michael cascade for the construction of the isochroman scaffold, a one‐pot deprotection/spiroacetalization operation for the formation of the tetracyclic core structure, and a late‐stage Ni‐catalyzed reductive coupling for the introduction of the lateral chain. Notably, four stereocenters are established from a single existing chiral center with excellent stereocontrol during the deprotection/spiroacetalization process. Stereocontrol of the intriguing deprotection/spiroacetalization process is supported by DFT calculations.
A concise total synthesis of (−)‐berkelic acid in eight linear steps was developed. This synthesis features a Catellani reaction/oxa‐Michael cascade for the construction of the isochroman scaffold, a one‐pot deprotection/spiroacetalization operation for the formation of tetracyclic core structure, and a late‐stage Ni‐catalyzed reductive coupling for the introduction of the lateral chain. |
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| AbstractList | Reported here is a concise total synthesis of (-)-berkelic acid in eight linear steps. This synthesis features a Catellani reaction/oxa-Michael cascade for the construction of the isochroman scaffold, a one-pot deprotection/spiroacetalization operation for the formation of the tetracyclic core structure, and a late-stage Ni-catalyzed reductive coupling for the introduction of the lateral chain. Notably, four stereocenters are established from a single existing chiral center with excellent stereocontrol during the deprotection/spiroacetalization process. Stereocontrol of the intriguing deprotection/spiroacetalization process is supported by DFT calculations. Reported here is a concise total synthesis of (−)‐berkelic acid in eight linear steps. This synthesis features a Catellani reaction/oxa‐Michael cascade for the construction of the isochroman scaffold, a one‐pot deprotection/spiroacetalization operation for the formation of the tetracyclic core structure, and a late‐stage Ni‐catalyzed reductive coupling for the introduction of the lateral chain. Notably, four stereocenters are established from a single existing chiral center with excellent stereocontrol during the deprotection/spiroacetalization process. Stereocontrol of the intriguing deprotection/spiroacetalization process is supported by DFT calculations. Reported here is a concise total synthesis of (-)-berkelic acid in eight linear steps. This synthesis features a Catellani reaction/oxa-Michael cascade for the construction of the isochroman scaffold, a one-pot deprotection/spiroacetalization operation for the formation of the tetracyclic core structure, and a late-stage Ni-catalyzed reductive coupling for the introduction of the lateral chain. Notably, four stereocenters are established from a single existing chiral center with excellent stereocontrol during the deprotection/spiroacetalization process. Stereocontrol of the intriguing deprotection/spiroacetalization process is supported by DFT calculations.Reported here is a concise total synthesis of (-)-berkelic acid in eight linear steps. This synthesis features a Catellani reaction/oxa-Michael cascade for the construction of the isochroman scaffold, a one-pot deprotection/spiroacetalization operation for the formation of the tetracyclic core structure, and a late-stage Ni-catalyzed reductive coupling for the introduction of the lateral chain. Notably, four stereocenters are established from a single existing chiral center with excellent stereocontrol during the deprotection/spiroacetalization process. Stereocontrol of the intriguing deprotection/spiroacetalization process is supported by DFT calculations. Reported here is a concise total synthesis of (−)‐berkelic acid in eight linear steps. This synthesis features a Catellani reaction/oxa‐Michael cascade for the construction of the isochroman scaffold, a one‐pot deprotection/spiroacetalization operation for the formation of the tetracyclic core structure, and a late‐stage Ni‐catalyzed reductive coupling for the introduction of the lateral chain. Notably, four stereocenters are established from a single existing chiral center with excellent stereocontrol during the deprotection/spiroacetalization process. Stereocontrol of the intriguing deprotection/spiroacetalization process is supported by DFT calculations. A concise total synthesis of (−)‐berkelic acid in eight linear steps was developed. This synthesis features a Catellani reaction/oxa‐Michael cascade for the construction of the isochroman scaffold, a one‐pot deprotection/spiroacetalization operation for the formation of tetracyclic core structure, and a late‐stage Ni‐catalyzed reductive coupling for the introduction of the lateral chain. |
| Author | Chen, Ruiming Wu, Chenggui Qu, Shuanglin Cao, Liming Tong, Wen‐Yan Wei, Qiang Wang, Qingqing Yang, Zhenjie Zhou, Qianghui Cheng, Hong‐Gang |
| Author_xml | – sequence: 1 givenname: Hong‐Gang orcidid: 0000-0001-9585-9093 surname: Cheng fullname: Cheng, Hong‐Gang organization: Wuhan University – sequence: 2 givenname: Zhenjie surname: Yang fullname: Yang, Zhenjie organization: Wuhan University – sequence: 3 givenname: Ruiming surname: Chen fullname: Chen, Ruiming organization: Wuhan University – sequence: 4 givenname: Liming surname: Cao fullname: Cao, Liming organization: Wuhan University – sequence: 5 givenname: Wen‐Yan surname: Tong fullname: Tong, Wen‐Yan organization: Hunan University – sequence: 6 givenname: Qiang surname: Wei fullname: Wei, Qiang organization: Wuhan University – sequence: 7 givenname: Qingqing surname: Wang fullname: Wang, Qingqing organization: Wuhan University – sequence: 8 givenname: Chenggui surname: Wu fullname: Wu, Chenggui organization: Wuhan University – sequence: 9 givenname: Shuanglin surname: Qu fullname: Qu, Shuanglin email: squ@hnu.edu.cn organization: Hunan University – sequence: 10 givenname: Qianghui orcidid: 0000-0002-8125-0380 surname: Zhou fullname: Zhou, Qianghui email: qhzhou@whu.edu.cn organization: Wuhan University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/33252181$$D View this record in MEDLINE/PubMed |
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| Keywords | FORMAL SYNTHESIS Catellani reaction reductive coupling KETONE FORMATION TETRACYCLIC CORE SPIROKETAL ALKYL-HALIDES CHAIN natural products TERTIARY ALKYL spiro-compounds COUPLING REACTIONS BERKELIC ACID ASSIGNMENT total synthesis |
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| Snippet | Reported here is a concise total synthesis of (−)‐berkelic acid in eight linear steps. This synthesis features a Catellani reaction/oxa‐Michael cascade for the... Reported here is a concise total synthesis of (-)-berkelic acid in eight linear steps. This synthesis features a Catellani reaction/oxa-Michael cascade for the... |
| Source | Web of Science |
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| StartPage | 5141 |
| SubjectTerms | Catellani reaction Chemical synthesis Chemistry Chemistry, Multidisciplinary natural products Physical Sciences reductive coupling Science & Technology spiro-compounds total synthesis |
| Title | A Concise Total Synthesis of (−)‐Berkelic Acid |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202014660 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000608302000001 https://www.ncbi.nlm.nih.gov/pubmed/33252181 https://www.proquest.com/docview/2491851184 https://www.proquest.com/docview/2465757667 |
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