A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicillin
[structures: see text] A short and efficient synthesis of the polyhydroxylated macrolactone (+)-aspicilin 1 using a stereoselective lithium perchlorate mediated addition of allyltributyltin to the equatorially disposed carboxaldehyde of 3 (derived from (R',R',R,S) butane diacetal protected...
| Váldodahkkit: | , , |
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| Materiálatiipa: | Journal article |
| Giella: | English |
| Almmustuhtton: |
2000
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| _version_ | 1826271633560567808 |
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| author | Dixon, D Foster, A Ley, S |
| author_facet | Dixon, D Foster, A Ley, S |
| author_sort | Dixon, D |
| collection | OXFORD |
| description | [structures: see text] A short and efficient synthesis of the polyhydroxylated macrolactone (+)-aspicilin 1 using a stereoselective lithium perchlorate mediated addition of allyltributyltin to the equatorially disposed carboxaldehyde of 3 (derived from (R',R',R,S) butane diacetal protected butane tetrol 2) as the key step is described. Terminal group manipulation and Masamune-Roush olefination using phosphonate ester 4 followed by macrocyclization via ring closing metathesis afforded the natural product after partial hydrogenation and global deprotection. |
| first_indexed | 2024-03-06T21:59:43Z |
| format | Journal article |
| id | oxford-uuid:4e2a0eb3-db43-4bc1-bf16-86b3b0c73edc |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T21:59:43Z |
| publishDate | 2000 |
| record_format | dspace |
| spelling | oxford-uuid:4e2a0eb3-db43-4bc1-bf16-86b3b0c73edc2022-03-26T15:59:38ZA short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicillinJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:4e2a0eb3-db43-4bc1-bf16-86b3b0c73edcEnglishSymplectic Elements at Oxford2000Dixon, DFoster, ALey, S[structures: see text] A short and efficient synthesis of the polyhydroxylated macrolactone (+)-aspicilin 1 using a stereoselective lithium perchlorate mediated addition of allyltributyltin to the equatorially disposed carboxaldehyde of 3 (derived from (R',R',R,S) butane diacetal protected butane tetrol 2) as the key step is described. Terminal group manipulation and Masamune-Roush olefination using phosphonate ester 4 followed by macrocyclization via ring closing metathesis afforded the natural product after partial hydrogenation and global deprotection. |
| spellingShingle | Dixon, D Foster, A Ley, S A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicillin |
| title | A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicillin |
| title_full | A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicillin |
| title_fullStr | A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicillin |
| title_full_unstemmed | A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicillin |
| title_short | A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicillin |
| title_sort | short and efficient stereoselective synthesis of the polyhydroxylated macrolactone aspicillin |
| work_keys_str_mv | AT dixond ashortandefficientstereoselectivesynthesisofthepolyhydroxylatedmacrolactoneaspicillin AT fostera ashortandefficientstereoselectivesynthesisofthepolyhydroxylatedmacrolactoneaspicillin AT leys ashortandefficientstereoselectivesynthesisofthepolyhydroxylatedmacrolactoneaspicillin AT dixond shortandefficientstereoselectivesynthesisofthepolyhydroxylatedmacrolactoneaspicillin AT fostera shortandefficientstereoselectivesynthesisofthepolyhydroxylatedmacrolactoneaspicillin AT leys shortandefficientstereoselectivesynthesisofthepolyhydroxylatedmacrolactoneaspicillin |