Synthesis 2014; 46(14): 1908-1916
DOI: 10.1055/s-0033-1339126
special topic
© Georg Thieme Verlag Stuttgart · New York

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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Weitere Informationen

Publikationsverlauf

Received: 17. März 2014

Accepted after revision: 05. Mai 2014

Publikationsdatum:
21. Mai 2014 (online)


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.

Supporting Information

 
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