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Synlett 2023; 34(17): 1961-1977
DOI: 10.1055/a-2068-7126
DOI: 10.1055/a-2068-7126
account
Synthesis of Natural Products, Carbocycles, and Heterocycles by Hauser–Kraus Annulation
I.N.N.N. thanks SERB India for financial support for research in the area of Hauser-Kraus Chemistry.
Abstract
In this Account, we summarize recent developments in Hauser–Kraus (H–K) annulation with respect to syntheses of natural products and other functionalized, fused, or spiro carbocycles and heterocycles. Although the classical H–K annulation occurs between a 1,4-dipolar synthon (a 3-nucleophilic phthalide), and a 1,2-dipolar synthon (a Michael acceptor), alternative modes of annulation, such as [4+4] and [4+1], as well as other reactivities of 3-nucleophilic phthalides that have been reported in recent years, are also covered in this account.
1 Introduction
2 Hauser–Kraus Annulation in Total Syntheses
3 Hauser–Kraus Annulation Methodologies
3.1 [4+2] Annulation
3.2 [4+4] Annulation Followed by Rearrangement
3.3 Michael Addition Followed by E2 Elimination
4 Miscellaneous Reactions
5 Conclusions
Key words
phthalides - Hauser–Kraus annulation - natural products - Dieckmann cyclization - spiro compounds - cascade reactionsPublication History
Received: 12 March 2023
Accepted after revision: 04 April 2023
Accepted Manuscript online:
04 April 2023
Article published online:
23 May 2023
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