Unified Synthesis of (–)-Folicanthine and (–)-Ditryptophenaline Enabled by a Room Temperature Nickel-Mediated Reductive Dimerization

Long Luo; Jian-Jian Zhang; Wei-Jian Ling; Yong-Liang Shao; Ya-Wen Wang; Yu Peng

doi:10.1055/s-0033-1339126

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(14): 1908-1916
DOI: 10.1055/s-0033-1339126

special topic

Unified Synthesis of (–)-Folicanthine and (–)-Ditryptophenaline Enabled by a Room Temperature Nickel-Mediated Reductive Dimerization

Long Luo

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China Fax: +86(931)8912586 eMail: pengyu@lzu.edu.cn

,

Jian-Jian Zhang

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China Fax: +86(931)8912586 eMail: pengyu@lzu.edu.cn

,

Wei-Jian Ling

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China Fax: +86(931)8912586 eMail: pengyu@lzu.edu.cn

,

Yong-Liang Shao

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China Fax: +86(931)8912586 eMail: pengyu@lzu.edu.cn

,

Ya-Wen Wang

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China Fax: +86(931)8912586 eMail: pengyu@lzu.edu.cn

,

Yu Peng*

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China Fax: +86(931)8912586 eMail: pengyu@lzu.edu.cn

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Abstract

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Abstract

A Ni·Phen-mediated reductive homocoupling of an optically active tertiary bromide has been efficiently achieved after the systematic screen of reaction conditions including ligands. This key step establishes sterically hindered vicinal quaternary stereocenters embedded in natural bispyrrolo[2,3-b]indoline alkaloids, thus enabling to realize the first asymmetric total synthesis of (–)-folicanthine via the detailed investigation of a challenging double decarboxylation. Notably, the concise synthesis of diketopiperazine alkaloid (–)-ditryptophenaline was also completed from the common dimeric intermediate.

Key words

nickel catalysis - reductive homocoupling - dimeric alkaloids - total synthesis - vicinal quaternary stereocenters

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Referenzen

References

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