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Total synthesis of (+)-alexine by utilizing a highly stereoselective 3+2 annulation reaction of an N-tosyl-alpha-amino aldehyde and a 1,3-bis(silyl)propene
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2008 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 14, no 10, 3072-3077 p.Article in journal (Refereed) Published
Abstract [en]

A novel route towards the polyhydroxylated pyrrolizidine alkaloid (+)-alexine has been developed. A key step in this synthesis is a highly stereoselective [3+2] annulation reaction of N-Ts-alpha-amino aldehyde 7a (Ts=tosyl) and 1,3-bis(silyl)propene 8a for the construction of the polyhydroxylated pyrrolidine subunit of the target molecule. Previous synthetic strategies rely on carbohydrates that require several protecting-group manipulations, thereby making the total number of steps relatively high. The [3+2] annulation strategy compares favorably with carbohydrate-based syntheses and constitutes a highly efficient entry to polyhydroxylated alkaloids.

Place, publisher, year, edition, pages
2008. Vol. 14, no 10, 3072-3077 p.
Identifiers
URN: urn:nbn:se:kth:diva-17450DOI: 10.1002/chem.200701776ISI: 000254872600014Scopus ID: 2-s2.0-53849084805OAI: oai:DiVA.org:kth-17450DiVA: diva2:335494
Note
QC 20100525Available from: 2010-08-05 Created: 2010-08-05 Last updated: 2017-12-12Bibliographically approved

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