Divergent Total Syntheses of C3a−C7′ Linked Diketopiperazine Alkaloids (+)‐Asperazine and (+)‐Pestalazine A Enabled by a Ni‐Catalyzed Reductive Coupling of Tertiary Alkyl Chloride

Short gram‐scale asymmetric syntheses of asperazine, pestalazine A, and their unnatural congeners thereof, have been achieved in ≈10 steps by using readily accessible starting materials. The nickel‐catalyzed reductive coupling protocol was utilized as a key step for the direct construction of C3asp3...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-01, Vol.25 (4), p.989-992
Main Authors: Long, Luo, Xiao‐Yong Zhai, Ya‐Wen Wang, Yu, Peng, Gong, Hegui
Format: Article
Language:English
Subjects:
Alkaloids
Chemistry
Congeners
Coupling
Nickel
Steric hindrance
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Summary:Short gram‐scale asymmetric syntheses of asperazine, pestalazine A, and their unnatural congeners thereof, have been achieved in ≈10 steps by using readily accessible starting materials. The nickel‐catalyzed reductive coupling protocol was utilized as a key step for the direct construction of C3asp3−C7′sp2 bond furnishing the diaryl‐substituted quaternary carbon centers with remarkable steric hindrance. The streamlined access to this core structure of heterodimeric tryptophans under the mild reaction conditions, makes this strategy hold a great promise in the concise synthesis of other relevant oligomeric pyrroloindoline alkaloids with unique C3a−C7′ linkages.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201805682