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Synlett 2020; 31(05): 403-420
DOI: 10.1055/s-0039-1690791
DOI: 10.1055/s-0039-1690791
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A Decade with Dötz Benzannulation in the Synthesis of Natural Products
Generous funding by the Department of Science & Technology, Science and Engineering Research Board (DST-SERB), New Delhi (Grant Nos. EMR/2017/000499 and SB/S1/OC-42/2013) is gratefully acknowledged. A.K. and R.S.P. thank the Indian Institute of Technology Bombay (IIT Bombay) for a senior research fellowship and a postdoctoral research fellowship, respectively.Further Information
Publication History
Received: 08 December 2019
Accepted after revision: 29 December 2019
Publication Date:
03 February 2020 (online)
‡ These authors contributed equally
Dedicated to Professor Reinhard Brückner (Albert-Ludwigs University Freiburg) on the occasion of his 64th birthday
Abstract
The Dötz benzannulation is a named reaction that utilizes Fischer chromium carbenes in a formal [3+2+1] cycloaddition with an alkyne and CO to produce the corresponding benzannulated product. Since its development in the 1970s, this reaction has been extensively used in the synthesis of natural products and various molecular architectures. Although the reaction sometimes suffers from the formation of other competing side products, the rapid construction of naphthol structures with a 1,4-dihydroxy unit makes it the most appropriate reaction for the synthesis of p-naphthoquinones. This review focuses on our group’s efforts over the past decade on the extensive use of this annulation reaction along with the contributions of others on the synthesis of different natural products.
1 Introduction
2 General Description and Mechanism of the Dötz Benzannulation Reaction
3 Applications of the Dötz Benzannulation in Natural Product Synthesis over the Last Decade
4 Conclusion
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