Robert M. Cory

Transformations of a macrocyclic cyclophane belt into advanced [8]cyclacene and [8]cyclacene triquinone precursors

Abstract Belt-shaped cyclophane 2 , is converted to a naphthalene-containing belt-shaped cyclophane by dehydrogenation, to an unexpected bisdiene-containing belt-shaped cyclophane by epoxidation and dehydration, and to an unexpected anthraquinone-containing belt-shaped cyclophane by PCC oxidation. The latter cyclophane could be functionalized further by a surprising oxidation involving sequential dehydrogenation and conjugate addition of ethoxide.

Macrocyclic cyclophane belts via double Diels-Alder cycloadditions: Macroannulation of bisdienes by bisdienophiles. Synthesis of a key precursor to an [8]cyclacene

Abstract A synthesis of macrocyclic cyclophanes is accomplished by double Diels-Alder cycloaddition of two bisdienophiles, 1,4,5,8-anthradiquinone and p -phenylenedimaleimide, to a bisdiene, 2,3,6,7-tetraheptylidene-1,2,3,4,5,6,7,8-octahydroanthracene. The structure of the macrocyclic cyclophane derived from the diquinone has been determined by single crystal x-ray diffraction, in addition to 1 H and 13 C NMR, HRMS and IR spectroscopic data.

A versatile synthesis of butenolides total synthesis of (+/-)-mintlactone

Abstract The butenolide monoterpenes, mintlactone and isomintlactone, have been synthesized by a new method for the preparation of butenolides from α, β-unsaturated esters by deconjugation, epoxidation and rearrangement.

Linearly fused ribbons of carbocyclic six-membered rings via Diels-Alder cycloadditions 1. Model studies and key intermediates

Abstract A synthesis of 7,14-dihexyl-6,15-hexacenedione is accomplished by Diels-Alder addition followed by dehydrogenation, and the double Diels-Alder components (1,4,5,8-anthradiquinone and 2,3,6,7-tetraheptylidene-1,2,3,4,5,6,7,8-octahydroanthracene) for a proposed synthesis of a cyclacene are prepared.

A divergent approach to patchouli sesquiterpenes : synthesis of 3-oxopatchouli alcohol, 5-oxo-7-hydroxy-13-norcycloseychellene, 6-methoxy-4,12-dehydro-13-norcycloseychellene and patchouli alcohol

Abstract α-Methylation of (−)-carvone followed by bicycloannulation with vinyltriphenylphosphonium bromide gives a 59% yield of a tricycio[3.2.1.0 2,7 ]octan-6-one which can be converted to precursors of (−)-patchouli alcohol, (−)-seychellene and (−)-cycloseycbellene.

Bicycloannulation: A one-step synthesis of tricyclo [3.2.1.02,7] octan-6-ones.

Die Cyclohexenone (I) werden mit Lithiumdiisopropylamid in die Lithiumenolate (II) ubergefuhrt, die durch Umsetzung mit dem Phosphoniumbromid (III) und anschliesendes Erhitzen in die Tricyclooctanone (IV) umgewandelt werden.

A short synthesis of ishwarone

Abstract 2,3,4-Trimethyl-2-cyclohexenone can be converted to the corresponding isoprene Diels-Alder adduct by a sequence initiated by conjugate addition of lithium bis(3-methyl-3-butenyl)cuprate; the sesquiterpenoid ishwarone has been synthesized in two steps from the resulting octalone.

Carbon Atom Insertion: A One-Step Synthesis of Tricyclo[3.2.1.02,7]octanes and Tricyclo[4.1.0.02,7]heptanes from Cyclohexenes1

Abstract Reinarz and Fonken have reported2 that the dibromocarbene adduct (1) of 1-methylcyclohexene, upon reaction with methylllthium at 0° in ether, produced exclusively the bicyclobutanes 2 and 3 in relative yields of 60% and 40%, respectively. We have prepared 1 by the phase-transfer method3 of Makosza and Fedorynski in a yield of 67%, found these previous results to be completely reproducible in our hands, and determined the combined yield of the two products (2 and 3) to be 67% also. Thus, the overall

Extended Chains of Six-Membered Rings 1. Model Studies and Key Intermediates

Abstract McMurry coupling of 4-phenylcyclohex-3-en-1-one and double addition of 1,4-dilithiobenzene and 4,4′-dilithiobiphenyl to cyclohexanones gives linear chains of three or four six-membered carbocyclic rings, including a potential intermediate in a proposed synthesis of [O6]paracyclophane.

Carbon atom insertion: an efficient synthesis of ishwarane1

A short total synthesis of the sesquiterpene ishwarane has been achieved using, as the key step, carbon atom insertion with carbon tetrabromide and methyl-lithium to form the tricyclo[3.2.1.02,7]octane ring system of the natural product.