A directed metalation route to the zwitterionic indole alkaloids.
Year: 1988
Type: article
Abstract: A synyhesis protocol involving beta-lithiation of 2-(2-pyridinyl)indoles (4 → 5) and subsequent reaction with bromoacetaldehyde leads to the indol[2,3-a]quinolzine(1)ring system. Application of this methodology to 2-(2-pyridinyl)indole 17, which is prepered via Taylor-Boger triazine Dieis-Alder annulation chemistry, affords the zwitterionic indole alkaloid sempervirine (3).
Source: Tetrahedron
Institution: Dartmouth College
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $3,680
OpenAlex ID: W1534697474