Synthesis of the (-)-TAN-2483B ring system via a D-mannose-derived cyclopropane.

Synthesis of C-furanosides from a D-glucal-derived cyclopropane through a ring-expansion/ring-contraction sequence.

gem-Dibromocyclopropane 1, prepared from tri-O-benzyl-D-glucal, undergoes thermal and silver-promoted ring expansion in the presence of alcohols to give substituted oxepines. With further heating, ring contraction to highly substituted tetrahydrofurans follows. These represent C-furanosides, potentially useful as precursors to C-nucleosides and other carbohydrate mimics.

Cyclopropane Fatty Acid Derivatives: Biosynthesis, Function and Total Synthesis

INTRODUCTION Cyclopropane-containing natural products are very unique owing to their unusual bonding and inherent ring strain (27.5 kcal/mol). 1 This strained ring has been found in naturally occurring terpenes, steroids, amino acids, fatty acids, alkaloids, and nucleic acids. For example, chrysanthemic acid derivatives, produced in plants via isoprenoid pathway are precursors to potent insecti...

Total Synthesis of Lycopalhine A.

The total synthesis of lycopalhine A has been accomplished. The synthesis features construction of the tricyclic system via cleavage of a cyclopropane ring and an ensuing intramolecular Michael addition, stereoselective introduction of a 2-aminoethyl moiety via a reaction of allyltrimethylsilane to a sulfonyliminium ion, and a stereoselective intramolecular aldol reaction.

Small ring analogs of acetylcholine. Synthesis and absolute configurations of cyclopropane derivatives.

AN APPROACH TO THE A RING OF VITAMIN D ANALOGUES VIA SEQUENTIAL CARBOMETALATION/ ANION CAPTURE

An intramolecular palladium catalysed carbometalation followed by anion capture achieves construction of a model comprised of the A ring of Vitamin D oxygen analogues.