Ernst Schering Foundation Symposium Proceedings, Vol. 2, pp. 125–139
DOI 10.1007/2789_2007_066
© Springer-Verlag Berlin Heidelberg
Published Online: 18 December 2007
Organocatalytic Syntheses
of Bioactive Natural Products
M. Christmann
(u)
Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
email: christmann@oc.rwth-aachen.de
1
Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 125
2
UCS1025A . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 126
3
Lepidopteran Sex Pheromones . . . . . . . . . . . . . . . . . . . 133
4
N-Heterocycles . . . . . . . . . . . . . . . . . . . . . . . . . . . 135
5
Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 136
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 136
Abstract. The current scope and limitations of organocatalytic reactions and
the consequences for the strategic planning of natural product syntheses are
discussed. Examples from our group include the total synthesis of UCS1025A
and lepidopteran sex pheromones.
1
Introduction
Natural product synthesis and medicinal chemistry exist in a symbiotic relationship with the development of synthesis methodology. Noyori’s asymmetric hydrogenations, Sharpless’ olefin oxidations, Grubbs’
olefin metathesis, Buchwald-Hartwig couplings and Jacobsen’s hydrolytic kinetic resolution are illustrious examples with many practical applications. The key to the success of the above-mentioned reactions is
that they have provided reliable shortcuts to more traditional synthetic
DOI 10.1007/2789_2007_066
© Springer-Verlag Berlin Heidelberg
Published Online: 18 December 2007
Organocatalytic Syntheses
of Bioactive Natural Products
M. Christmann
(u)
Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
email: christmann@oc.rwth-aachen.de
1
Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 125
2
UCS1025A . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 126
3
Lepidopteran Sex Pheromones . . . . . . . . . . . . . . . . . . . 133
4
N-Heterocycles . . . . . . . . . . . . . . . . . . . . . . . . . . . 135
5
Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 136
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 136
Abstract. The current scope and limitations of organocatalytic reactions and
the consequences for the strategic planning of natural product syntheses are
discussed. Examples from our group include the total synthesis of UCS1025A
and lepidopteran sex pheromones.
1
Introduction
Natural product synthesis and medicinal chemistry exist in a symbiotic relationship with the development of synthesis methodology. Noyori’s asymmetric hydrogenations, Sharpless’ olefin oxidations, Grubbs’
olefin metathesis, Buchwald-Hartwig couplings and Jacobsen’s hydrolytic kinetic resolution are illustrious examples with many practical applications. The key to the success of the above-mentioned reactions is
that they have provided reliable shortcuts to more traditional synthetic