A synthetic strategy based on the application of three consecutive ring-expansion
reactions has been used in the synthesis of analogues of the macrocyclic core of the
solomonamide natural products. Starting from a simple, readily available tetrahydrocarbazole,
oxidative ring expansion is followed by two further 3- and 4-atom ring-expansion reactions,
enabling the insertion of amino acid and hydroxy acid derived linear fragments into
15- to 17-membered-ring-enlarged macrocyclic products.
Key words
macrocycles - medium-sized rings - ring expansion - natural product analogues - lactams
- lactones - solomonamides