Total Synthesis of the Alleged Structure of (+)-Fimbricalyxoid A
An enantioselective total synthesis of the alleged structure of (+)-fimbricalyxoid A is reported. The synthetic strategy features a pyridine-N-oxidate-mediated SN2' reaction to introduce an oxygen functionality at position C3 of the A-ring and a sequential three-step process via the cleavage of the C-O bonds and hemiketalization to form the 3,20-oxybridge. With this strategy, the target molecule was synthesized in 19% overall yield and 12 steps from our previously synthesized cis-fused octahydrophenanthrene (+)-6.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:24 |
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| Enthalten in: |
Organic letters - 24(2022), 19 vom: 20. Mai, Seite 3477-3481 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Li, Lin-Ping [VerfasserIn] |
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| Links: |
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| Themen: |
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| Anmerkungen: |
Date Completed 23.05.2022 Date Revised 17.06.2022 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.orglett.2c01076 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM340505699 |
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| 245 | 1 | 0 | |a Total Synthesis of the Alleged Structure of (+)-Fimbricalyxoid A |
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| 500 | |a Date Revised 17.06.2022 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a An enantioselective total synthesis of the alleged structure of (+)-fimbricalyxoid A is reported. The synthetic strategy features a pyridine-N-oxidate-mediated SN2' reaction to introduce an oxygen functionality at position C3 of the A-ring and a sequential three-step process via the cleavage of the C-O bonds and hemiketalization to form the 3,20-oxybridge. With this strategy, the target molecule was synthesized in 19% overall yield and 12 steps from our previously synthesized cis-fused octahydrophenanthrene (+)-6 | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 700 | 1 | |a Han, Jia-Qi |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Fan |e verfasserin |4 aut | |
| 700 | 1 | |a Wu, Xiong |e verfasserin |4 aut | |
| 700 | 1 | |a Xie, Jian-Hua |e verfasserin |4 aut | |
| 700 | 1 | |a Zhou, Qi-Lin |e verfasserin |4 aut | |
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