Stereoselective synthesis of octahydrocyclohepta[c]pyran-6(1H)-one scaffolds through a Prins/alkynylation/hydration sequence
Aldehydes undergo a smooth coupling with (E/Z)-non-3-en-8-yn-1-ol in the presence of 10 mol% of CuX and BF3·OEt2 under mild conditions to produce a novel class of octahydrocyclohepta[c]pyran-6(1H)-one derivatives in good yields with excellent diastereoselectivity through a sequential Prins/alkynylat...
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| Published in: | Organic & biomolecular chemistry Vol. 13; no. 40; p. 10212 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
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England
28-10-2015
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| Abstract | Aldehydes undergo a smooth coupling with (E/Z)-non-3-en-8-yn-1-ol in the presence of 10 mol% of CuX and BF3·OEt2 under mild conditions to produce a novel class of octahydrocyclohepta[c]pyran-6(1H)-one derivatives in good yields with excellent diastereoselectivity through a sequential Prins/alkynylation/hydration. This is the first report on the termination of Prins cyclization with a tethered alkyne. |
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| AbstractList | Aldehydes undergo a smooth coupling with (E/Z)-non-3-en-8-yn-1-ol in the presence of 10 mol% of CuX and BF3·OEt2 under mild conditions to produce a novel class of octahydrocyclohepta[c]pyran-6(1H)-one derivatives in good yields with excellent diastereoselectivity through a sequential Prins/alkynylation/hydration. This is the first report on the termination of Prins cyclization with a tethered alkyne. |
| Author | Reddy, B V Subba Venkateswarlu, A Kunwar, Ajit C Kanakaraju, M |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26308943$$D View this record in MEDLINE/PubMed |
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| Snippet | Aldehydes undergo a smooth coupling with (E/Z)-non-3-en-8-yn-1-ol in the presence of 10 mol% of CuX and BF3·OEt2 under mild conditions to produce a novel class... |
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| SubjectTerms | Aldehydes - chemistry Alkynes - chemistry Cyclization Cycloheptanes - chemical synthesis Cycloheptanes - chemistry Molecular Conformation Pyrones - chemical synthesis Pyrones - chemistry Stereoisomerism |
| Title | Stereoselective synthesis of octahydrocyclohepta[c]pyran-6(1H)-one scaffolds through a Prins/alkynylation/hydration sequence |
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