An efficient synthesis of loline alkaloids

Mesut Cakmak, Peter Mayer, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

Loline (1) is a small alkaloid that, in spite of its simple-looking structure, has posed surprising challenges to synthetic chemists. It has been known for more than a century and has been the subject of extensive biological investigations, but only two total syntheses have been achieved to date. Here, we report an asymmetric total synthesis of loline that, with less then ten steps, is remarkably short. Our synthesis incorporates a Sharpless epoxidation, a Grubbs olefin metathesis and an unprecedented transannular aminobromination, which converts an eight-membered cyclic carbamate into a bromopyrrolizidine. The synthesis is marked by a high degree of chemo- and stereoselectivity and gives access to several members of the loline alkaloid family. It delivers sufficient material to support a programme aimed at studying the complex interactions between plants, fungi, insects and bacteria brokered by loline alkaloids.

Original languageEnglish (US)
Pages (from-to)543-545
Number of pages3
JournalNature Chemistry
Volume3
Issue number7
DOIs
StatePublished - May 2011

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Alkaloids
Stereoselectivity
Carbamates
Epoxidation
Alkenes
Fungi
Olefins
Bacteria
loline

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Cakmak, M., Mayer, P., & Trauner, D. (2011). An efficient synthesis of loline alkaloids. Nature Chemistry, 3(7), 543-545. https://doi.org/10.1038/nchem.1072

An efficient synthesis of loline alkaloids. / Cakmak, Mesut; Mayer, Peter; Trauner, Dirk.

In: Nature Chemistry, Vol. 3, No. 7, 05.2011, p. 543-545.

Research output: Contribution to journalArticle

Cakmak, M, Mayer, P & Trauner, D 2011, 'An efficient synthesis of loline alkaloids', Nature Chemistry, vol. 3, no. 7, pp. 543-545. https://doi.org/10.1038/nchem.1072
Cakmak, Mesut ; Mayer, Peter ; Trauner, Dirk. / An efficient synthesis of loline alkaloids. In: Nature Chemistry. 2011 ; Vol. 3, No. 7. pp. 543-545.
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