Divergent Total Syntheses of C3 a−C7′ Linked Diketopiperazine Alkaloids (+)‐Asperazine and (+)‐Pestalazine A Enabled by a Ni‐Catalyzed Reductive Coupling of Tertiary Alkyl Chloride
Authors:
- 17 November 2018
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 25 (4) , 989-992
Abstract
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.Keywords
Funding Information
- National Natural Science Foundation of China (21472075, 21572140, 21772078)
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