Studies on Oxidopyrylium [5 + 2] Cycloadditions:  Toward a General Synthetic Route to the C12-Hydroxy Daphnetoxins

12-Hydroxydaphnetoxins, members of the structurally fascinating daphnane diterpene family, exhibit a wide range of significant biological activities. A general route to the BC-ring system of 12-hydroxy daphnetoxins is reported based on d-ribose. Depending on the choice of protecting groups and solve...

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Published inOrganic letters Vol. 8; no. 23; pp. 5373 - 5376
Main Authors Wender, Paul A, Bi, F. Christopher, Buschmann, Nicole, Gosselin, Francis, Kan, Cindy, Kee, Jung-Min, Ohmura, Hirofumi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 09.11.2006
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ENANTIOPURE
TUMOR PROMOTERS
ASYMMETRIC INDUCTION
RING
(+)-RESINIFERATOXIN
ALDOL REACTIONS
PHORBOL
STEREOSELECTIVE-SYNTHESIS
DAPHNANE
DITERPENE
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Summary:12-Hydroxydaphnetoxins, members of the structurally fascinating daphnane diterpene family, exhibit a wide range of significant biological activities. A general route to the BC-ring system of 12-hydroxy daphnetoxins is reported based on d-ribose. Depending on the choice of protecting groups and solvent, the oxidopyrylium−alkene [5 + 2] cycloaddition originating from A provides cycloadduct diastereomer B or C with good to excellent selectivity.
Bibliography:Medline
NIH RePORTER
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062234e