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The total synthesis of (−)-aplysin via a lithiation–borylation–propenylation sequence
A concise, highly enantioselective synthesis of sesquiterpene natural products (−)-debromoaplysin and (−)-aplysin has been completed. The key steps included lithiation–borylation of a secondary benzylic carbamate to give a tertiary boronic ester followed by propenylation which installed the quaterna...
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| Published in: | Tetrahedron 2012-09, Vol.68 (37), p.7598-7604 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c360t-e25d16071ba10afaad9b00245a47e5b5d387fc3325c37cd08ea5798521a25de3 |
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| cites | cdi_FETCH-LOGICAL-c360t-e25d16071ba10afaad9b00245a47e5b5d387fc3325c37cd08ea5798521a25de3 |
| container_end_page | 7604 |
| container_issue | 37 |
| container_start_page | 7598 |
| container_title | Tetrahedron |
| container_volume | 68 |
| creator | Fletcher, Catherine J. Blair, Daniel J. Wheelhouse, Katherine M.P. Aggarwal, Varinder K. |
| description | A concise, highly enantioselective synthesis of sesquiterpene natural products (−)-debromoaplysin and (−)-aplysin has been completed. The key steps included lithiation–borylation of a secondary benzylic carbamate to give a tertiary boronic ester followed by propenylation which installed the quaternary stereocenter with complete enantioselectivity. Subsequent RCM followed by deprotection and in situ cyclization led to debromoaplysin with good diastereoselectivity from which the target compound was prepared in just eight overall steps.
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| doi_str_mv | 10.1016/j.tet.2012.05.095 |
| format | article |
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| identifier | ISSN: 0040-4020 |
| ispartof | Tetrahedron, 2012-09, Vol.68 (37), p.7598-7604 |
| issn | 0040-4020 1464-5416 |
| language | eng |
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| source | ScienceDirect Journals |
| subjects | Alicyclic compounds, terpenoids, prostaglandins, steroids Aplysin B derivatives Chemistry Esters Exact sciences and technology Lithiation–borylation Natural products Noncondensed benzenic compounds Organic chemistry Organometalloidal and organometallic compounds Preparations and properties Quaternary stereocenter RCM Sesquiterpene Synthesis Terpenoids Tetrahedrons Total synthesis |
| title | The total synthesis of (−)-aplysin via a lithiation–borylation–propenylation sequence |
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