Biomimetic Organic Synthesis by Erwan Poupon, Bastien Nay

By Erwan Poupon, Bastien Nay

During this fascinating 2 quantity set, the process and method of bio-inspired synthesis of complicated normal items is laid out, subsidized by way of considerable useful examples from the authors' personal paintings in addition to from the broadcast literature.

Volume 1 describes the biomimetic synthesis of alkaloids.

Volume 2 covers terpenes, polyketides, and polyphenols.

A dialogue of the present demanding situations and frontiers in biomimetic synthesis concludes this accomplished handbook.

Key features:

  • Biomimetic suggestions became an every-day software not just for chemists but in addition for biologists. the substitute functions are overwhelming, making this accomplished 2 quantity paintings a must have for everybody operating within the field.
  • Unifying either artificial and biosynthetic features, this publication covers every thing from organocatalysis and typical product synthesis to man made biology or even eco-friendly chemistry.

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Example text

Decarboalkoxylation in strong acidic conditions was accompanied with dehydration at position 7 and gave rise to (±)-elaeokanine A (90) in 91% yield. Milder conditions were necessary to carry out the synthesis of (±)-elaeokanine C (84). The conditions were carefully studied by the authors, who finally chose catalytic transfer hydrogenation with ammonium formate and palladium in methanol to afford the desired reaction. Although some degree of selectivity was expected, the outcome of the reaction clearly showed a preference for the wrong isomer, with a predominance of (±)-7-epi-elaeokanine C (91) over (±)-elaeokanine C (84) despite a good overall yield of 60% from bis-acetal 79.

This experiment and its outcome in terms of stereochemistry can be rationalized when considering transition state 92 in which an equatorial hydroxyl is to be expected. This supposition was compared to a similar case studied by Tufariello and Ali [50] a few years before with the intramolecular kinetic aldol reaction of a ketone instead of a β-ketoester. In the latter, a stereocontrol, totally in favor of the axial configuration, could have been governed by transition state 93. Returning to a biosynthesis hypothesis and taking into account these findings, one can suggest that should such a pathway occur in Nature the decarboxylation step has to be prior to the aldol reaction.

L-Lysine (l-3) (l-Lys, K): is the only amino acid to have two different biosynthetic pathways. One is the aspartate (5) pathway present in bacteria, plants, and algae. The other starts from α-ketoglutarate (6) and is present in fungi [3, 4]. Lysine is an essential amino acid for humans. 1 reflects some of the biochemical relations between l-ornithine (l-1)/l-arginine (l-2) and l-lysine (l-3). 2) Only important metabolic intermediates, helpful for a better comprehension of the following sections, have been stressed.

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