Recent developments of stereoselective biocatalytic and chemocatalytic methods are discussed. The review provides a guide to the use of biocatalytic methods in the area of chemical synthesis with focused attention on retrosynthetic considerations and analysis. The transformations presented are organized according to bond disconnections and attendant synthetic methods. The review is expected to lead to better understanding of the characteristics and distinctions of the two complementary approaches. It depicts for researchers in bio- and chemocatalysis a road map of challenges and opportunities for the evolution (and at times revolution) in chemical synthesis.
In diesem Aufsatz werden neue Entwicklungen auf den Gebieten der biokatalytischen und chemokatalytischen Synthese diskutiert. Der Beitrag soll als Anleitung für die Verwendung biokatalytischer Methoden in der chemischen Synthese dienen, insbesondere bei retrosynthetischen Überlegungen und Analysen. Die Gliederung dieses Aufsatzes ist nach den Bindungsknüpfungen und ihren jeweiligen synthetischen Methoden strukturiert.
The first total synthesis of nominal harziane diterpenoid 1 is disclosed, whose spectral characteristics did not match those of the reported natural product. Stereochemical analysis and subsequent synthesis of the epimeric tertiary alcohol led to reassignment of configuration of the natural product as shown for 2. At the heart of the synthesis is an enyne cycloisomerization that sets a key quaternary stereocenter within a cyclobutane with high diastereocontrol. The route features strategies for the synthesis of the highly congested 6‐5‐7‐4 carbon skeleton characteristic of the caged harziane diterpenoids.
A novel Lewis acid-catalyzed cycloisomerization of alkylidenecyclopropane acylsilanes is disclosed that involves tandem Prins addition/ring expansion/1,2-silyl shift to grant access to bicyclo[4.2.0]octanes and bicyclo[3.2.0]heptanes.
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