A. M. Viljoen scite author profile

The pentacycloundecane (PCU) cage structure resembles a perfect boat conformation, and for the first time unique lactam/lactone interconversions on the flagpole carbons of a cyclohexane boat structure are reported. The syntheses of a novel dihydroxy-PCU-delta-lactone and two novel N-substituted PCU-delta-lactams are reported. Hydrolysis of some of the PCU-delta-lactam compounds produced delta-lactones, and reaction of the lactones with ammonia or primary amines again produced delta-lactams. Reaction mechanisms to account for the unusual interconversion reactions induced by transannular interactions are proposed.

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The dimerization and photochemical rearrangement of pentacyclo-[5.4.0.02,6.03,10.05,9]undecane-8-thione

Read¹,

Martins²,

Viljoen³

2004

Tetrahedron Letters

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A. M. Viljoen

Enantioselective synthesis of amino acids from pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione

Synthesis of 8,11-dihydroxy-pentacyclo[5.4.0.02,6.03,10.05,9]Undecane-8,11-lactam

Synthesis of δ-lactams from pentacyclo[5.4.0.02,6.03,10.05,9]Undecane-8,11-dione

Complete ¹H and ¹³C NMR spectral assignment of pentacyclo [6.4.0.0^2,6.0^5,9.0^4,12]dodecane derivatives and structure elucidation of pentacyclo [6.4.0.0^2,6.0^3,11.0^5,9]dodecane

The influence of hydrate formation on the Clemmensen reduction of pentacyclo [5.4.0.02,6.03,10.05,9]undecane-8,11-dione and pentacyclo[6.4.0.02,7.03,11.06,10]dodecane-9,12-dione

Synthesis of 4-oxahexacyclo[5.4.1.02,6.03,10.05,9.08,11]dodecane-3-carboxylic acid

Interconvertions between δ-Lactam and δ-Lactone Derivatives Initiated by Unique Transannular Interactions of the Rigid Cyclohexane Boat Structure in Pentacycloundecane

The dimerization and photochemical rearrangement of pentacyclo-[5.4.0.02,6.03,10.05,9]undecane-8-thione

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A. M. Viljoen

Enantioselective synthesis of amino acids from pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione

Synthesis of 8,11-dihydroxy-pentacyclo[5.4.0.02,6.03,10.05,9]Undecane-8,11-lactam

Synthesis of δ-lactams from pentacyclo[5.4.0.02,6.03,10.05,9]Undecane-8,11-dione

Complete 1H and 13C NMR spectral assignment of pentacyclo [6.4.0.02,6.05,9.04,12]dodecane derivatives and structure elucidation of pentacyclo [6.4.0.02,6.03,11.05,9]dodecane

The influence of hydrate formation on the Clemmensen reduction of pentacyclo [5.4.0.02,6.03,10.05,9]undecane-8,11-dione and pentacyclo[6.4.0.02,7.03,11.06,10]dodecane-9,12-dione

Synthesis of 4-oxahexacyclo[5.4.1.02,6.03,10.05,9.08,11]dodecane-3-carboxylic acid

Interconvertions between δ-Lactam and δ-Lactone Derivatives Initiated by Unique Transannular Interactions of the Rigid Cyclohexane Boat Structure in Pentacycloundecane

The dimerization and photochemical rearrangement of pentacyclo-[5.4.0.02,6.03,10.05,9]undecane-8-thione

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Complete ¹H and ¹³C NMR spectral assignment of pentacyclo [6.4.0.0^2,6.0^5,9.0^4,12]dodecane derivatives and structure elucidation of pentacyclo [6.4.0.0^2,6.0^3,11.0^5,9]dodecane