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Asymmetric Synthesis of (−)-6-Desmethyl-Fluvirucinine A(1) via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions
The versatile synthesis of (−)-6-desmethyl-fluvirucinine A(1) was accomplished at a 24% overall yield through a thirteen-step process from a known vinylpiperidine. The key part involved the elaboration of the distal stereocenters and a macrolactam skeleton via conformationally-induced diastereocontr...
| Autores principales: | , , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
MDPI
2018
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6225218/ https://www.ncbi.nlm.nih.gov/pubmed/30223428 http://dx.doi.org/10.3390/molecules23092351 |
| _version_ | 1783369725491806208 |
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| author | Moon, Hyunyoung Yoon, Hojong Lim, Changjin Jang, Jaebong Yi, Jong-Jae Lee, Jae Kyun Lee, Jeeyeon Na, Younghwa Son, Woo Sung Kim, Seok-Ho Suh, Young-Ger |
| author_facet | Moon, Hyunyoung Yoon, Hojong Lim, Changjin Jang, Jaebong Yi, Jong-Jae Lee, Jae Kyun Lee, Jeeyeon Na, Younghwa Son, Woo Sung Kim, Seok-Ho Suh, Young-Ger |
| author_sort | Moon, Hyunyoung |
| collection | PubMed |
| description | The versatile synthesis of (−)-6-desmethyl-fluvirucinine A(1) was accomplished at a 24% overall yield through a thirteen-step process from a known vinylpiperidine. The key part involved the elaboration of the distal stereocenters and a macrolactam skeleton via conformationally-induced diastereocontrol and the iterative aza-Claisen rearrangements of lactam precursors. |
| format | Online Article Text |
| id | pubmed-6225218 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2018 |
| publisher | MDPI |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-62252182018-11-13 Asymmetric Synthesis of (−)-6-Desmethyl-Fluvirucinine A(1) via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions Moon, Hyunyoung Yoon, Hojong Lim, Changjin Jang, Jaebong Yi, Jong-Jae Lee, Jae Kyun Lee, Jeeyeon Na, Younghwa Son, Woo Sung Kim, Seok-Ho Suh, Young-Ger Molecules Article The versatile synthesis of (−)-6-desmethyl-fluvirucinine A(1) was accomplished at a 24% overall yield through a thirteen-step process from a known vinylpiperidine. The key part involved the elaboration of the distal stereocenters and a macrolactam skeleton via conformationally-induced diastereocontrol and the iterative aza-Claisen rearrangements of lactam precursors. MDPI 2018-09-14 /pmc/articles/PMC6225218/ /pubmed/30223428 http://dx.doi.org/10.3390/molecules23092351 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
| spellingShingle | Article Moon, Hyunyoung Yoon, Hojong Lim, Changjin Jang, Jaebong Yi, Jong-Jae Lee, Jae Kyun Lee, Jeeyeon Na, Younghwa Son, Woo Sung Kim, Seok-Ho Suh, Young-Ger Asymmetric Synthesis of (−)-6-Desmethyl-Fluvirucinine A(1) via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions |
| title | Asymmetric Synthesis of (−)-6-Desmethyl-Fluvirucinine A(1) via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions |
| title_full | Asymmetric Synthesis of (−)-6-Desmethyl-Fluvirucinine A(1) via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions |
| title_fullStr | Asymmetric Synthesis of (−)-6-Desmethyl-Fluvirucinine A(1) via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions |
| title_full_unstemmed | Asymmetric Synthesis of (−)-6-Desmethyl-Fluvirucinine A(1) via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions |
| title_short | Asymmetric Synthesis of (−)-6-Desmethyl-Fluvirucinine A(1) via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions |
| title_sort | asymmetric synthesis of (−)-6-desmethyl-fluvirucinine a(1) via conformationally-controlled diastereoselective lactam-ring expansions |
| topic | Article |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6225218/ https://www.ncbi.nlm.nih.gov/pubmed/30223428 http://dx.doi.org/10.3390/molecules23092351 |
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