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Resolution of an iridoid synthon, gastrolactol, by means of dynamic acetylation and lipase-catalyzed alcoholysis
KTH, Sweden.
KTH, Sweden.
KTH, Sweden.
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2001 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 66, no 16, 5384-5387 p.Article in journal (Refereed) Published
Abstract [en]

A short synthetic route to asymmetric iridoids was developed. The three key steps were an intramolecular [4 + 2] cycloaddition reaction of an enamine derivative of 8-oxocitral (2), a dynamic acetylation, and an enzymatic resolution of the gastrolactyl acetates 5a and 5b, iridoids with three stereocenters. Some regio- and stereoselective heterogeneous catalytic hydrogenations of double bonds in iridoid aglucones were discussed.

Place, publisher, year, edition, pages
2001. Vol. 66, no 16, 5384-5387 p.
Keyword [en]
aphid sex-pheromone, actinidia-polygama, glucosides, stereochemistry, biosynthesis, iridolactones, chemistry, cultures, cataria, glands
National Category
Natural Sciences
Research subject
Natural Science, Ecological chemistry
Identifiers
URN: urn:nbn:se:lnu:diva-14120ISI: 000170301200014OAI: oai:DiVA.org:lnu-14120DiVA: diva2:440779
Note

460HB Times Cited:6 Cited References Count:49

Available from: 2011-09-13 Created: 2011-09-13 Last updated: 2017-01-11Bibliographically approved

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Unelius, C. Rikard
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