A Case for Bond-Network Analysis in the Synthesis of Bridged Polycyclic Complex Molecules: Hetidine and Hetisine Diterpenoid Alkaloids.

Autor: Doering NA; Latimer Hall, Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA., Sarpong R; Latimer Hall, Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA., Hoffmann RW; Fachbereich Chemie der Philipps Universität Marburg, 35032, Marburg, Germany.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2020 Jun 26; Vol. 59 (27), pp. 10722-10731. Date of Electronic Publication: 2020 Apr 15.
DOI: 10.1002/anie.201909656
Abstrakt: A key challenge in the synthesis of diterpenoid alkaloids lies in identifying strategies that rapidly construct their multiply bridged polycyclic skeletons. Existing approaches to these structurally intricate secondary metabolites are discussed in the context of a "bond-network analysis" of molecular frameworks, which was originally devised by Corey some 40 years ago. The retrosynthesis plans that emerge from a topological analysis of the highly bridged frameworks of the diterpenoid alkaloids are discussed in the context of eight recent syntheses of hetidine and hetisine natural products and their derivatives. This Minireview highlights the extent to which network analyses of the type described here sufficed for designing synthesis plans, as well as areas where they had to be amalgamated with functional group oriented synthetic planning considerations.
(© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.)
Databáze: MEDLINE
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