Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 174-192 |
| Seitenumfang | 19 |
| Fachzeitschrift | SYNLETT |
| Ausgabenummer | 2 |
| Publikationsstatus | Veröffentlicht - Jan. 2009 |
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.
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Organische Chemie
Zitieren
- Standard
- Harvard
- Apa
- Vancouver
- BibTex
- RIS
in: SYNLETT, Nr. 2, 01.2009, S. 174-192.
Publikation: Beitrag in Fachzeitschrift › Übersichtsarbeit › Forschung › Peer-Review
}
TY - JOUR
T1 - Highly stereoselective aldol reactions in the total syntheses of complex natural products
AU - Brodmann, Tobias
AU - Lorenz, Michael
AU - Schäckel, Romy
AU - Simsek, Serkan
AU - Kalesse, Markus
PY - 2009/1
Y1 - 2009/1
N2 - 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.
AB - 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.
KW - Aldol reactions
KW - Natural product synthesis
KW - Stereoselectivity
KW - Vinylogy
UR - http://www.scopus.com/inward/record.url?scp=62349099126&partnerID=8YFLogxK
U2 - 10.1055/s-0028-1087520
DO - 10.1055/s-0028-1087520
M3 - Review article
AN - SCOPUS:62349099126
SP - 174
EP - 192
JO - SYNLETT
JF - SYNLETT
SN - 0936-5214
IS - 2
ER -