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Concise synthesis of calystegines B2 and B3via intramolecular Nozaki-Hiyama-Kishi reaction.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2016 Jun 07; Vol. 14 (21), pp. 4885-96. Date of Electronic Publication: 2016 May 10. - Publication Year :
- 2016
-
Abstract
- The key step in the concise syntheses of calystegine B2 and its C-2 epimer calystegine B3 was the construction of cycloheptanone 8via an intramolecular Nozaki-Hiyama-Kishi (NHK) reaction of 9, an aldehyde containing a Z-vinyl iodide. Vinyl iodide 9 was obtained by the Stork olefination of aldehyde 10, derived from carbohydrate starting materials. Calystegines B2 (3) and B3 (4) were synthesized from d-xylose and l-arabinose derivatives respectively in 11 steps in excellent overall yields (27% and 19%).
- Subjects :
- Aldehydes chemistry
Chemistry Techniques, Synthetic
Cycloheptanes chemistry
Enzyme Inhibitors pharmacology
Glycoside Hydrolases antagonists & inhibitors
Nortropanes pharmacology
Solanaceous Alkaloids pharmacology
Stereoisomerism
Enzyme Inhibitors chemical synthesis
Enzyme Inhibitors chemistry
Nortropanes chemical synthesis
Nortropanes chemistry
Solanaceous Alkaloids chemical synthesis
Solanaceous Alkaloids chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 14
- Issue :
- 21
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 27161660
- Full Text :
- https://doi.org/10.1039/c6ob00697c