Abstract
The first total synthesis of the enantiomer of the indolizidine alkaloid, cyclizidine, was accomplished from readily available d-serine as the starting chiron. The relevant key reactions involve the stereocontrolled construction of the indolizidine ring system with the required functionality and further elaboration to install the cyclopropyl dienyl side chain. With this total synthesis, the absolute configuration of the natural product based on a redetermination of its X-ray structure has been confirmed.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Alkaloids / chemical synthesis*
-
Alkaloids / chemistry
-
Alkaloids / pharmacology*
-
Anti-Bacterial Agents / chemical synthesis*
-
Anti-Bacterial Agents / chemistry
-
Anti-Bacterial Agents / pharmacology*
-
Crystallography, X-Ray
-
Indolizidines / chemical synthesis*
-
Indolizidines / chemistry
-
Indolizidines / pharmacology*
-
Indolizines / chemistry
-
Molecular Conformation
-
Molecular Structure
-
Serine / analogs & derivatives
-
Serine / chemistry
-
Stereoisomerism
Substances
-
Alkaloids
-
Anti-Bacterial Agents
-
Indolizidines
-
Indolizines
-
ent-cyclizidine
-
Serine
-
indolizomycin