TY - JOUR
T1 - Lessons and revelations from biomimetic syntheses
AU - Razzak, Mina
AU - De Brabander, Jef K.
N1 - Funding Information:
Our successful synthesis of berkelic acid, based on the combination of the o-quinone methide tautomer of pulvilloric acid (75) and a hydrated spicifernin (74), led us to question whether nature produces berkelic acid in the same way. This hypothesis was supported by the isolation of spiciferone A (73) from the same Berkeley Pit Penicillium strain that produces berkelic acid. Spicifernin and spiciferone A have previously been co-isolated
PY - 2011/12
Y1 - 2011/12
N2 - Biomimetic synthesis describes the field of organic chemistry that aims to emulate the natural, biosynthetic processes toward natural products. As well as providing insight into how molecules are formed in nature, the benefits of this approach to total synthesis are numerous and extend beyond the gains typical of traditional synthesis. For example, using biosynthetic proposals to design a synthetic route can highlight alternative methods to the desired target. The pursuit of biomimetic syntheses also promotes the development of new reactions to prove or disprove a biosynthetic proposal or to unravel mechanistic implications of a proposed biosynthesis and can lead to the identification of new natural products. Here we look at some recent compelling examples and examine how biomimetic synthesis has led to the discovery of new procedures and principles that would not have been found by other approaches.
AB - Biomimetic synthesis describes the field of organic chemistry that aims to emulate the natural, biosynthetic processes toward natural products. As well as providing insight into how molecules are formed in nature, the benefits of this approach to total synthesis are numerous and extend beyond the gains typical of traditional synthesis. For example, using biosynthetic proposals to design a synthetic route can highlight alternative methods to the desired target. The pursuit of biomimetic syntheses also promotes the development of new reactions to prove or disprove a biosynthetic proposal or to unravel mechanistic implications of a proposed biosynthesis and can lead to the identification of new natural products. Here we look at some recent compelling examples and examine how biomimetic synthesis has led to the discovery of new procedures and principles that would not have been found by other approaches.
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U2 - 10.1038/nchembio.709
DO - 10.1038/nchembio.709
M3 - Review article
C2 - 22086288
AN - SCOPUS:81355123306
SN - 1552-4450
VL - 7
SP - 865
EP - 875
JO - Nature chemical biology
JF - Nature chemical biology
IS - 12
ER -