Polar Intramolecular Cross-Cycloadditions of Cyclopropanes toward Natural Product Synthesis

Zhongwen Wang

doi:10.1055/s-0032-1317082

Synlett, Table of Contents

Synlett 2012; 23(16): 2311-2327
DOI: 10.1055/s-0032-1317082

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Polar Intramolecular Cross-Cycloadditions of Cyclopropanes toward Natural Product Synthesis

Zhongwen Wang*

State Key Lab of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China, Fax: +86(22)23503627 Email: wzwrj@nankai.edu.cn

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Abstract

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Abstract

In this account we have systematically described the acid-promoted intramolecular cycloadditions of activated cyclopropanes, which were conceptually classified into intramolecular cross-cycloadditions (IMCC) and intramolecular parallel-cycloadditions. The IMCC provided a general and efficient strategy for construction of structurally complex and diverse bridged bicyclic skeletons. The potential of this strategy has been demonstrated by the synthesis of natural products.

1 Introduction

2 [3+2]IMCC of Cyclopropane 1,1-Diester with C=O

3 [3+2]IMCC of Cyclopropane 1,1-Diester with C=N

4 [3+2]IMCC of Cyclopropane 1,1-Diester with C=C

5 [3+3]IMCC of Cyclopropane 1,1-Diester with Nitrones

6 [3+2]IMCC of Mono-donor/Mono-acceptor Cyclopropane with C=O

7 Lewis Acid Regulated Domino Cycloisomerization/[4+2]IMCC or [3+2]IMCC of Alkynylcyclopropane Ketone with C=O and C=N

8 Conclusions and Outlook

Key words

cycloaddition - total synthesis - natural products - tandem reaction - ring opening

Full Text

References

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33 To be submitted
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36 Investigations on the [4+2]IMCC of functionalized cyclobutane are underway in our laboratory