Change search
ReferencesLink to record
Permanent link

Direct link
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.
URN: urn:nbn:se:kth:diva-17450DOI: 10.1002/chem.200701776ISI: 000254872600014ScopusID: 2-s2.0-53849084805OAI: diva2:335494
QC 20100525Available from: 2010-08-05 Created: 2010-08-05Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full textScopus

Search in DiVA

By author/editor
Somfai, Peter
By organisation
Organic Chemistry
In the same journal
Chemistry - A European Journal

Search outside of DiVA

GoogleGoogle Scholar
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

Altmetric score

Total: 23 hits
ReferencesLink to record
Permanent link

Direct link