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Herein, we describe a practical two-step synthesis of an Indolo[3,2-c]quinoline scaffold from substituted 4-methoxyquinolines using Fischer indole method and oxidative aromatization in one-pot under Microwave radiation. With this protocol, a biologically active natural product, Isocryptolepine, and its analogues can be readily and efficiently accessed. Also, this method has been efficiently utilized to generate a series of novel pyrrole-containing derivatives of this heterocyclic system.
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A pyrone remodeling strategy to access diverse heterocycles: application to the synthesis of fascaplysin natural products
The synthesis of diverse N -fused heterocycles, including the pyrido[1,2- a ]indole scaffold, using an efficient pyrone remodeling strategy is described. The pyrido[1,2- a ]indole core was demonstrated to be a versatile scaffold that can be site-selectively functionalized. The utility of this novel annulation strategy was showcased in a concise formal synthesis of three fascaplysin congeners.
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- Award ID(s):
- 1856228
- PAR ID:
- 10216657
- Date Published:
- Journal Name:
- Chemical Science
- Volume:
- 12
- Issue:
- 4
- ISSN:
- 2041-6520
- Page Range / eLocation ID:
- 1528 to 1534
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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- Free Publicly Accessible Full Text
-
Accepted Manuscript1.0
- Journal Article:
- https://doi.org/10.1039/D0SC06317G
