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...
Автори: | , , |
---|---|
Формат: | Journal article |
Мова: | English |
Опубліковано: |
2000
|
_version_ | 1826271633560567808 |
---|---|
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 |