Issue 64, 2020

Eight-step total synthesis of (+)-crambescin A

Abstract

(+)-Crambescin A belongs to the polycyclic guanidine natural product family and has been shown to possess various medically important properties. The chiral bicyclic guanidine structure of (+)-crambescin A presents a challenge for chemical synthesis. Here we implement a novel asymmetric Biginelli reaction strategy to achieve the enantiospecific total synthesis of (+)-crambescin A in only 8 steps from the abundant and inexpensive aliphatic aldehyde, urea and methyl 3-oxobutanoate.

Graphical abstract: Eight-step total synthesis of (+)-crambescin A

Supplementary files

Article information

Article type
Paper
Submitted
13 Oct 2020
Accepted
16 Oct 2020
First published
26 Oct 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 39266-39270

Eight-step total synthesis of (+)-crambescin A

Z. Gao, J. Li, Y. Song, X. Bi, X. Meng and Y. Guo, RSC Adv., 2020, 10, 39266 DOI: 10.1039/D0RA08726B

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