A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicillin

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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Dades bibliogràfiques
Autors principals: Dixon, D, Foster, A, Ley, S
Format: Journal article
Idioma:English
Publicat: 2000
Descripció
Sumari:[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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