TY - JOUR
T1 - Collective synthesis of natural products by means of organocascade catalysis
AU - Jones, Spencer B.
AU - Simmons, Bryon
AU - Mastracchio, Anthony
AU - MacMillan, David W.C.
N1 - Funding Information:
Acknowledgements Financial support was provided by NIHGMS (R01 GM078201-05) and gifts from Merck, Bristol-Myers Squibb and Abbott. S.B.J. and B.S. thank Bristol-Myers Squibb and Merck, respectively, for graduate fellowships.
PY - 2011/7/14
Y1 - 2011/7/14
N2 - Organic chemists are now able to synthesize small quantities of almost any known natural product, given sufficient time, resources and effort. However, translation of the academic successes in total synthesis to the large-scale construction of complex natural products and the development of large collections of biologically relevant molecules present significant challenges to synthetic chemists. Here we show that the application of two nature-inspired techniques, namely organocascade catalysis and collective natural product synthesis, can facilitate the preparation of useful quantities of a range of structurally diverse natural products from a common molecular scaffold. The power of this concept has been demonstrated through the expedient, asymmetric total syntheses of six well-known alkaloid natural products: strychnine, aspidospermidine, vincadifformine, akuammicine, kopsanone and kopsinine.
AB - Organic chemists are now able to synthesize small quantities of almost any known natural product, given sufficient time, resources and effort. However, translation of the academic successes in total synthesis to the large-scale construction of complex natural products and the development of large collections of biologically relevant molecules present significant challenges to synthetic chemists. Here we show that the application of two nature-inspired techniques, namely organocascade catalysis and collective natural product synthesis, can facilitate the preparation of useful quantities of a range of structurally diverse natural products from a common molecular scaffold. The power of this concept has been demonstrated through the expedient, asymmetric total syntheses of six well-known alkaloid natural products: strychnine, aspidospermidine, vincadifformine, akuammicine, kopsanone and kopsinine.
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U2 - 10.1038/nature10232
DO - 10.1038/nature10232
M3 - Article
C2 - 21753848
AN - SCOPUS:79960407415
SN - 0028-0836
VL - 475
SP - 183
EP - 188
JO - Nature
JF - Nature
IS - 7355
ER -