C. W. Murtiashaw

The ester enolate Claisen rearrangement. Synthesis of a C(1)-C(6) erythronolide fragment

Abstract An enantioselective route to the C(1)C(6) erythronolide unit 10 is described, involving the dioxanone-to-dihydropyran enolate Claisen rearrangement ( 7 → 8 ), regio- and stereoselective hydroboration to give 9a , and reductive fragmentation of the heterocyclic template ( 9c → 10 ).

Synthesis of optically active mevinic acid subunits via acetal initiated/vinylsilane terminated polyene cyclizations

Abstract Efficient routes to optically active octahydronaphthalenol mevinic acid subunits via vinylsilane-mediated polyene cyclizations initiated by trimethylenedioxy acetals are detailed. Enantioselective alkynone reductions and Ireland-Claisen rearrangements serve to establish and transfer absolute stereochemistry.

Synthetic studies directed at (±)-quadrone. A new end game.

Abstract A synthesis of (±quadrone ( 1 ) is described, featuring an intramolecular delivery of the C(6)-carbon, thus avoiding possible regio- and stereochemical complications in the δ-lactone construction.

Vinylsilane-mediated polyene cyclization. Synthesis of the octahydronaphthalenol portion of dihydrocompactin

Abstract A synthesis of the octahydronaphthalenol portion 12 of the HMG-CoA reductase inhibitor dihydrocompactin (1) is described wherein a vinylsilane-terminated polyene cyclization and variants of the Claisen rearrangement provide key elements of regio- and stereocontrol.