Zorana Ferjancic

Intermolecular free radical additions to strained cycloalkenes. Cyclopropene and cyclobutene as radical acceptors

Abstract Intermolecular additions of electrophilic radicals to cyclopropene and cyclobutene derivatives afford the addition products in 37–50% yield. The strain relief in the intermediary radical accelerates the addition, as shown by competitive addition experiments.

A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids

The design, synthesis and biological evaluation of a novel C,D-spirolactone analogue of paclitaxel is described. This is the first paclitaxel analogue without an oxetane D-ring that shows a significant cytotoxic effect (activity one order of magnitude lower than paclitaxel). More importantly, its cytotoxicity is a result of a different mechanism of action, involving mTOR inhibition-dependent autophagy instead of G(2)/M cell cycle arrest-dependent apoptosis.

Free radical mediated construction of small ring compounds: the double annulation of bicyclo[3.1.0]hex-2-enes

Abstract A free radical approach to fused cyclopropane derivatives is described. Homolytic decomposition of thiohydroxamic esters 4a-e in the presence of dimethyl acetylenedicarboxylate affords bicyclo[3.1.0]hex-2-enes 6a-e in moderate yields.

Total synthesis of (+)-swainsonine and (+)-8-epi-swainsonine

Enantioselective synthesis of (+)-swainsonine was achieved in 9 steps, with 24% overall yield. The key feature of the synthesis is the tactical combination of reactions: organocatalyzed aldolization/reductive amination, which allows for a rapid construction of highly functionalized heterocyclic systems. In a similar way (+)-8-epi-swainsonine was synthesized (7 steps, 28%).

Radical, one-step approach to o-chlorophenyl thioethers from xanthates. A rapid access to vinylsilanes.

Xanthates have been readily converted into o-chlorophenyl thioethers using a one-step procedure conducted under radical conditions. In some selected cases, these aryl thioethers were successfully oxidized to the corresponding sulfoxides and sulfenic acid elimination afforded the corresponding vinylsilanes.

Total Synthesis of (±)‐Alstoscholarisine A

The first total synthesis of the neuroactive indole alkaloid (±)-alstoscholarisine A is reported. The key step of the concise synthesis is an efficient domino sequence that was used to assemble the 2,8-diazabicyclo[3.3.1]nonane core through the formation of two C-N bonds and one C-C bond in a single step.