Highly stereoselective aldol reactions in the total syntheses of complex natural products

verfasst von: Tobias Brodmann, Michael Lorenz, Romy Schäckel, Serkan Simsek, Markus Kalesse
Abstract: More than ever, it is a challenging objective in synthetic chemistry to create efficient access to biologically active compounds. In particular, one structural element which is frequently incorporated in the framework of complex natural products is a β-hydroxy ketone. In this context, the aldol reaction as the most important transformation to generate this structural element not only creates new C-C bonds but also establishes stereogenic centers. In recent years, a large variety of highly selective methodologies for aldol and aldol-type reactions has been put forward. On this background, the vinylogous Mukaiyama aldol reaction became a pivotal transformation since it also allows for the immediate transformation of the olefin which is simultaneously introduced. This Account covers the application of various (vinylogous) aldol reactions from our laboratories in the syntheses of natural products with important biological activities. 1 Introduction 2 Polyketides: Selected Natural Products 3 Vinylogous Mukaiyama Aldol Reaction (VMAR) 3.1 Triarylboranes in the Substrate-Controlled VMAR in the Synthesis of Ratjadone 3.1.1 Suppression of the Silyl Cation Catalyzed Pathway 3.1.2 Substrate-Controlled VMAR in the Synthesis of Oleandolide 3.1.3 Substrate-Controlled VMAR in the Synthesis of Amphidinolide H2 and Tedanolide 3.2 Oxazaborolidinones as Chiral Lewis Acids in the Enantioselective VMAR 4 Aldol Reactions in Natural Product Syntheses 4.1 Tedanolide 4.2 Chivosazole 4.3 Disorazole 4.4 Epothilone 4.5 Spirangien 5 Conclusions and Outlook.
Organisationseinheit(en): Institut für Organische Chemie
Typ: Übersichtsarbeit
Journal: SYNLETT
Seiten: 174-192
Anzahl der Seiten: 19
ISSN: 0936-5214
Publikationsdatum: 01.2009
Publikationsstatus: Veröffentlicht
Peer-reviewed: Ja
ASJC Scopus Sachgebiete: Organische Chemie
Elektronische Version(en): https://doi.org/10.1055/s-0028-1087520 (Zugang: Unbekannt)

BibTeX

@article{a113bc190a684a1a9b4e7b437c70bc06,
title = "Highly stereoselective aldol reactions in the total syntheses of complex natural products",
abstract = "More than ever, it is a challenging objective in synthetic chemistry to create efficient access to biologically active compounds. In particular, one structural element which is frequently incorporated in the framework of complex natural products is a β-hydroxy ketone. In this context, the aldol reaction as the most important transformation to generate this structural element not only creates new C-C bonds but also establishes stereogenic centers. In recent years, a large variety of highly selective methodologies for aldol and aldol-type reactions has been put forward. On this background, the vinylogous Mukaiyama aldol reaction became a pivotal transformation since it also allows for the immediate transformation of the olefin which is simultaneously introduced. This Account covers the application of various (vinylogous) aldol reactions from our laboratories in the syntheses of natural products with important biological activities. 1 Introduction 2 Polyketides: Selected Natural Products 3 Vinylogous Mukaiyama Aldol Reaction (VMAR) 3.1 Triarylboranes in the Substrate-Controlled VMAR in the Synthesis of Ratjadone 3.1.1 Suppression of the Silyl Cation Catalyzed Pathway 3.1.2 Substrate-Controlled VMAR in the Synthesis of Oleandolide 3.1.3 Substrate-Controlled VMAR in the Synthesis of Amphidinolide H2 and Tedanolide 3.2 Oxazaborolidinones as Chiral Lewis Acids in the Enantioselective VMAR 4 Aldol Reactions in Natural Product Syntheses 4.1 Tedanolide 4.2 Chivosazole 4.3 Disorazole 4.4 Epothilone 4.5 Spirangien 5 Conclusions and Outlook.",
keywords = "Aldol reactions, Natural product synthesis, Stereoselectivity, Vinylogy",
author = "Tobias Brodmann and Michael Lorenz and Romy Sch{\"a}ckel and Serkan Simsek and Markus Kalesse",
year = "2009",
month = jan,
doi = "10.1055/s-0028-1087520",
language = "English",
pages = "174--192",
journal = "SYNLETT",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "2",
}