Classical Methods in Structure Elucidation of Natural Products
The structures of many natural products are given in
standard textbooks on organic chemistry as 'established facts'. Yet for those
natural products whose structures were determined between 1860 and 1960 by
classical chemical methods, the lines of evidence are frequently buried under
any number of investigations that led to dead ends and to revised structure
assignments. Since very little is known about the structure clarification of
these products at present, this volume serves to shed light once again on the
achievements of previous generations of chemists, who worked with minimal
The selection of the 25 representative examples is subjective and arbitrary,
dictated by the author's pleasure in recovering fundamental milestones in
organic chemistry, with each chapter devoted to one organic compound. The time
period covered, however, is more precisely defined: 1860 represents the advent
of structure theory, prior to which there was no conceptual framework to address
the 'structure' of a compound. One hundred years later, 1960 approximately marks
the change from classical structure elucidation to the era in which structure
elucidation is mainly based on spectroscopic evidence and X-ray crystallography.
Since the emphasis of this work is on classical structure elucidation, work
performed later than 1960 is only considered in exceptional cases.
Rather than simply provide a history of structure elucidation of particular
natural products, the author combines results from historic experiments to trace
a line of evidence for those structures that are nowadays accepted as
established. This line of evidence may follow the path put forward by the
original contributors, yet in some cases the experimental facts have been
combined to form another, hopefully shorter, line of evidence. As a result,
readers are able to ascertain for themselves the 'facts behind the established
structure assignments' of a number of important natural products.
COMPOUNDS WITH ONLY OXYGEN FUNCTIONALITIES
COMPOUNDS WITH NITROGEN AND OXYGEN FUNCTIONALITIES
COMPOUNDS WITH ADDITIONAL FUNCTIONALITIES
COMPOUNDS WITHOUT HETEROATOM-FUNCTIONALITIES
CAN YOU DO IT YOURSELF?