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Org Biomol Chem. 2021 Feb 18;19(6):1395-1403. doi: 10.1039/d0ob02527e.

Exploiting an intramolecular Diels-Alder cyclization/dehydro-aromatization sequence for the total syntheses of ellipticines and calothrixin B.

Organic & biomolecular chemistry

Chengdan Deng, Yuancui Liu, Mei Xu, Kaiqiang Xie, Sheng Liu

Affiliations

  1. State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, China. [email protected] and Key Laboratory of Chemistry for Natural Products of Guizhou Province, Chinese Academy of Sciences, Guiyang 550014, China. [email protected].
  2. Key Laboratory of Chemistry for Natural Products of Guizhou Province, Chinese Academy of Sciences, Guiyang 550014, China. [email protected].

PMID: 33491728 DOI: 10.1039/d0ob02527e

Abstract

The tetracyclic and pentacyclic skeletons of pyrido and quinolinocarbazole alkaloids have been synthesized via a unified strategy. The prominent key step involved a Diels-Alder intramolecular cyclization/dehydro-aromatization sequence. From these carbazole-lactam cores, linear syntheses have been developed for ellipticines and calothrixin B.

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