Abstract
Pyrroloiminoquinone alkaloids represent a structurally intriguing class of natural products that display an array of useful biological properties. Here, we present a versatile and scalable platform for the synthesis of this diverse family – and in particular the antitumor discorhabdins – built upon sequential selective C–H functionalization of tryptamine. The utility of this strategy is showcased through short formal syntheses of damirones A–C, makaluvamines D and I, and discorhadbin E. Additionally, we describe efforts to develop the first catalytic asymmetric entry to the discorhabdin subclass.
Original language | English (US) |
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Pages (from-to) | 3366-3370 |
Number of pages | 5 |
Journal | Tetrahedron |
Volume | 75 |
Issue number | 24 |
DOIs | |
State | Published - Jun 14 2019 |
Externally published | Yes |
Keywords
- Alkaloids
- C–H functionalization
- Natural products
- Total synthesis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry