Synthetic Studies towards the Total Synthesis of Indole Alkaloids Containing Indolyl Lactam Frameworks

Dong-Xing Tan; Fu-She Han

doi:10.1055/s-0040-1706480

Synlett, Table of Contents

Synlett 2021; 32(07): 663-673
DOI: 10.1055/s-0040-1706480

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Synthetic Studies towards the Total Synthesis of Indole Alkaloids Containing Indolyl Lactam Frameworks

Dong-Xing Tan

^aCAS Key Lab of High-Performance Synthetic Rubber and its Composite Materials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Jilin 130022, P. R. of China Email: fshan@ciac.ac.cn

^bUniversity of Science and Technology of China, Hefei, Anhui 230026, P. R. of China

,

Fu-She Han∗

^aCAS Key Lab of High-Performance Synthetic Rubber and its Composite Materials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Jilin 130022, P. R. of China Email: fshan@ciac.ac.cn

^bUniversity of Science and Technology of China, Hefei, Anhui 230026, P. R. of China

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Abstract

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Abstract

In this account, recent progress on the synthetic studies of several monoterpene indole alkaloids, (±)-mersicarpine, misassigned (±)-tronoharine, and (±)-leuconodines D and E, is summarized. Specifically, the rationale for the design and development of the Lewis acid catalyzed S_N1-type substitution and formal [3+3] cycloaddition reaction of indol-2-yl carbinols, and the Pd-catalyzed aerobic oxidative intramolecular Heck cross-coupling of indolyl amides tethered with a terminal olefin functionality, are emphasized. These key reactions set the basis for the rapid construction of the fused ring skeleton containing an all-carbon quaternary center at the indol-2-yl position.

1 Introduction

2 Synthetic Study of (±)-Mersicarpine

3 Synthetic Study of the Misassigned (±)-Tronoharine

4 Study of the Asymmetric Reaction of Indol-2-yl Carbinols

5 Synthetic Study of (±)-Leuconodines D and E

6 Conclusion

Key words

synthesis - indole alkaloid - mersicarpine - tronoharine - leuconodine - indolyl carbinol - oxidative Heck coupling

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References

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