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...

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Автори: Dixon, D, Foster, A, Ley, S
Формат: Journal article
Мова:English
Опубліковано: 2000
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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.
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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