Synthesis and studies of marine natural products: the dictyoxetane core from 8-oxabicyclo[3.2.1]oct-6-en-3-ones

Starting from functionalized 8-oxabicyclo[3.2.1]oct-6-en-3-one rac- 3 a series of tricyclic epoxy alcohols ( 4 , and aminated derivative 16 ) have been prepared. After some tuning of the oxygen and nitrogen protecting group at carbon C3 with respect to steric bulk, stability and lipophilicity the hi...

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Bibliographic Details
Published in:Tetrahedron 2002-07, Vol.58 (31), p.6199-6206
Main Authors: Proemmel, S, Wartchow, R, Hoffmann, H.M.R
Format: Article
Language:English
Subjects:
6,8-dimethyl-2,7-dioxatricyclo[4.2.1.0 3,8]nonane
anti-tumor
tricyclic oxetanes
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Summary:Starting from functionalized 8-oxabicyclo[3.2.1]oct-6-en-3-one rac- 3 a series of tricyclic epoxy alcohols ( 4 , and aminated derivative 16 ) have been prepared. After some tuning of the oxygen and nitrogen protecting group at carbon C3 with respect to steric bulk, stability and lipophilicity the highly functionalized tricyclic oxetanes 5 and 17 are accessible in short synthetic order. The structure of key dioxatricycles 9b and 17 has been corroborated by X-ray crystal diffraction analysis. Biological activities have been evaluated. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00622-1