Efficient Synthesis of the Structural Core of Tetracyclines by a Palladium-Catalyzed Domino Tsuji-Trost-Heck-Mizoroki Reaction

The Pd‐catalyzed domino Tsuji–Trost–Heck–Mizoroki reactions of compounds 18, 27, and 34, respectively, each containing an allyl acetate and a halogen aryl moiety, lead to the formation of hexahydronaphthacenes 2 and 3 and octahydroanthracene 4 in 62–81 % yield. The octahydroanthracene and hexahydron...

Full description

Saved in:

Bibliographic Details
Published in:	Chemistry : a European journal Vol. 14; no. 8; pp. 2527 - 2535
Main Authors:	Tietze, Lutz F., Redert, Thomas, Bell, Hubertus P., Hellkamp, Sascha, Levy, Laura M.
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 07-03-2008 WILEY‐VCH Verlag
Subjects:	antibiotics Benzyl Compounds - chemistry Catalysis domino reactions Ether - chemistry metathesis Molecular Structure palladium Palladium - chemistry tetracyclines Tetracyclines - chemical synthesis Tetracyclines - chemistry
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Description
Summary:	The Pd‐catalyzed domino Tsuji–Trost–Heck–Mizoroki reactions of compounds 18, 27, and 34, respectively, each containing an allyl acetate and a halogen aryl moiety, lead to the formation of hexahydronaphthacenes 2 and 3 and octahydroanthracene 4 in 62–81 % yield. The octahydroanthracene and hexahydronaphthacene motifs are found in many natural products, for example, the tetracycline antibiotics. Multiple‐ring synthesis: Hexahydronaphthacenes and octahydroanthracenes can be formed by a palladium‐catalyzed domino Tsuji–Trost–Heck–Mizoroki reaction with starting materials that contain an allyl acetate and a halogen aryl moiety (see scheme; dppe: 1,2‐bis(diphenylphosphino)ethane). The octahydroanthracene and hexahydronaphthacene motifs are found in many natural products, such as the tetracycline antibiotics.
Bibliography:	Deutsche Forschungsgemeinschaft Stiftung Stipendienfonds des Verbandes der Chemischen Industrie ArticleID:CHEM200701676 istex:67D643C5B0F72115D69277182D52F7A8F1D64EA5 Studienstiftung des deutschen Volkes ark:/67375/WNG-RW3TSNDB-L EC ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0947-6539 1521-3765
DOI:	10.1002/chem.200701676