Synthesis of the C4-C16 Polyketide Fragment of Portimines A and B
Stereoselective synthesis of the C4-C16 polyketide fragment of portimines A and B is reported, enabled by our previously established method for the stereoselective synthesis of syn-α,α'-dihydroxyketones. The preparation of this advanced fragment provides insights useful for the total synthesis of portimines A and B. An asymmetric Evans aldol reaction was used to install the C10-C11 adjacent stereogenic centers before incorporation of indantrione, followed by epoxidation and epoxide opening to forge the challenging syn-α,α'-dihydroxyketone functionality.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:86 |
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| Enthalten in: |
The Journal of organic chemistry - 86(2021), 18 vom: 17. Sept., Seite 12840-12850 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Ding, Xiao-Bo [VerfasserIn] |
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| Links: |
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| Themen: |
Epoxy Compounds |
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| Anmerkungen: |
Date Completed 22.10.2021 Date Revised 22.10.2021 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/acs.joc.1c01463 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM330122304 |
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| 500 | |a Date Revised 22.10.2021 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Stereoselective synthesis of the C4-C16 polyketide fragment of portimines A and B is reported, enabled by our previously established method for the stereoselective synthesis of syn-α,α'-dihydroxyketones. The preparation of this advanced fragment provides insights useful for the total synthesis of portimines A and B. An asymmetric Evans aldol reaction was used to install the C10-C11 adjacent stereogenic centers before incorporation of indantrione, followed by epoxidation and epoxide opening to forge the challenging syn-α,α'-dihydroxyketone functionality | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 7 | |a Epoxy Compounds |2 NLM | |
| 650 | 7 | |a Imines |2 NLM | |
| 650 | 7 | |a Polyketides |2 NLM | |
| 650 | 7 | |a Spiro Compounds |2 NLM | |
| 650 | 7 | |a portimine |2 NLM | |
| 700 | 1 | |a Aitken, Harry R M |e verfasserin |4 aut | |
| 700 | 1 | |a Pearl, Esperanza S |e verfasserin |4 aut | |
| 700 | 1 | |a Furkert, Daniel P |e verfasserin |4 aut | |
| 700 | 1 | |a Brimble, Margaret A |e verfasserin |4 aut | |
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