General Preparation and Controlled Cyclization of Acyclic Terpenoids
A general preparation method of the all-(E)-polyprenols 12 has been developed from readily available geranyl sulfone by the chain-extension process utilizing the C5 unit 5 and the chain-termination process utilizing the C5 unit 10 together with the chemoselective reductive desulfonylation. The polyp...
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Veröffentlicht in: | Journal of organic chemistry 2008-03, Vol.73 (5), p.1991-1994 |
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Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | A general preparation method of the all-(E)-polyprenols 12 has been developed from readily available geranyl sulfone by the chain-extension process utilizing the C5 unit 5 and the chain-termination process utilizing the C5 unit 10 together with the chemoselective reductive desulfonylation. The polyprenols 12 were converted to compounds 3 containing two consecutive prenyl sulfone moieties at the tail end, which underwent the controlled electrophilic cyclization only at the carbon−carbon double bonds that were remote from the flat and rigid benzenesulfonyl groups. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo702303a |