An extremely short way to prostaglandins has been opened by combining the newly devised organometallic methodologies. Convergent, one-pot creation of the prostanoid framework is achieved by organocopper conjugate addition of the S-configurated ω-side-chain unit to (R)-4-trialkylsiloxy-2-cyclopentenone followed by the organotin-aided trapping of the enolate intermediate by α-side-chain alkyl iodides. Prostaglandin E
2
can be prepared in only three steps from the chiral building units. The protected 5,6-didehydro-PGE
2
derivatives thus obtained serve as common intermediates for the synthesis of a variety of naturally occurring prostaglandins including prostacyclin. This approach is also useful for the controlled synthesis of isocarbacyclin.
Enantioselective Radical Addition/Cross‐Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents