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Synthesis 2017; 49(19): 4383-4413
DOI: 10.1055/s-0036-1590870
DOI: 10.1055/s-0036-1590870
review
Recent Advances on the Application of Electrocyclic Reactions in Complex Natural Product Synthesis
We are grateful to Zhejiang Natural Science Fund for Distinguished Young Scholars (LR16B020001), the NSFC (21302204, 21472167, 21622205) and Fundamental Research Funds for the Central Universities (2017XZZX002-02) for financial support.Weitere Informationen
Publikationsverlauf
Received: 14. März 2017
Accepted after revision: 08. Mai 2017
Publikationsdatum:
24. August 2017 (online)
Abstract
The electrocyclic reaction is one of the most powerful tools for the construction of complex polycyclic scaffolds in a highly stereocontrolled fashion. In this review, recent advances in its application in the total synthesis of representative natural products are discussed, with the aim of providing a complement to existing reviews.
1 Introduction
2 4π Electrocyclization
2.1 Neutral 4π Electrocyclization
2.2 Cationic 4π Electrocyclization
3 6π Electrocyclization
3.1 All-Carbon 6π Electrocyclization
3.2 Oxa-6π Electrocyclization
3.3 Aza-6π Electrocyclization
3.4 Retro-6π Electrocyclization
4 8π Electrocyclization
5 Conclusion and Outlook
-
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For representative investigations on the solvent effects of the electrocyclization, see:
For reviews on electrocyclic reactions, see:
For related reviews on Nazarov cyclization, see:
For a recent review on the cyclobutenes, see:
For recent studies on cyclobutenes, see:
For application of cyclobutenes, see:
For a recent review on the derivatives of podophyllotoxin, see:
For reviews, see:
For the selected examples, see:
For isolations, see:
For the bioactivities of its derivatives, see:
For recent studies on 1-aminopentadienyl species in aza-Nazarov reactions, see:
For a recent example on 3-aminopentadienyl cation in aza-Nazarov cyclization, see:
For selected examples on Nazarov reactions initiated by conjugated addition, see:
For recent studies on Nazarov reactions initiated by cascade rearrangements, see:
For reviews on Piancatelli rearrangements, see:
For other plausible mechanisms of Piancatelli rearrangements, see:
For azides:
For halides:
For amines:
For others:
For reviews on formal homo-Nazarov reactions, see:
For recent applications in total synthesis, see:
For recent applications in aza-6π cyclization to pyridine frameworks, see:
For syntheses of hainanolidol and harringtonolide, see:
For syntheses of colchicine, see:
For the synthesis of salvileucalin B, see:
For recent reviews on the synthesis of strychnine, see:
For tricyclooctene skeletons, see:
For bicyclic octadiene skeletons, see: