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- Title
Biosynthetically Relevant Reactivity of Polyneuridine Aldehyde.
- Authors
Turpin, Victor; Poupon, Erwan; Jullian, Jean‐Christophe; Evanno, Laurent
- Abstract
Polyneuridine aldehyde is a key intermediate in the biosynthetic routes of monoterpene indole alkaloids family of natural products. The molecule is the first biosynthetic member of the sarpagan‐type alkaloids and is an entry to the ajmalan‐type and alstophyllan‐type alkaloids. Complementary to the recent description of polyneuridine aldehyde, its reactivity was studied. Retro‐biomimetic formation of corynan‐type alkaloids (e.g., geissoschizine) and the biomimetic formation of quebrachidine, the first biosynthetic parent of the ajamalan‐type alkaloids, were performed. In addition, an unusual intramolecular carbonyl‐ene‐reaction involving the indole nucleus delivered an original polycyclic scaffold.
- Subjects
ALDEHYDE reactivity; INDOLE alkaloids; ENE reactions; NATURAL products; BIRTHPARENTS
- Publication
European Journal of Organic Chemistry, 2020, Vol 2020, Issue 45, p6989
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202000963