Nothing Special   »   [go: up one dir, main page]

Magnus et al., 1987 - Google Patents

Stereospecific dicobalt octacarbonyl mediated enyne cyclization for the synthesis of the cytotoxic sesquiterpene (.+-.)-quadrone

Magnus et al., 1987

Document ID
873027484337547504
Author
Magnus P
Principe L
Slater M
Publication year
Publication venue
The Journal of Organic Chemistry

External Links

Snippet

Ethyl isobutyrate was converted into theenyne 20, through a straightforward sequence of transformations. Treatment of 20 with Co2 (CO) 8/CO/86 C, in the presence of 2, 6-di-ferf- butyl-4-methylpyridine (0.1 equiv), gave the bicyclo [3.3. 0] enone 25 (45%), in a completely …
Continue reading at pubs.acs.org (other versions)

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/41Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587Unsaturated compounds containing a keto groups being part of a ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/48Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
    • C07C29/50Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2101/00Systems containing only non-condensed rings
    • C07C2101/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2101/16The ring being unsaturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D221/00Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D317/00Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D497/00Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/30Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2103/00Systems containing at least three condensed rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides

Similar Documents

Publication Publication Date Title
Magnus et al. Stereospecific dicobalt octacarbonyl mediated enyne cyclization for the synthesis of the cytotoxic sesquiterpene (.+-.)-quadrone
Still Stannylation/destannylation. New syntheses of carbonyl compounds via organotin intermediates
Stork et al. Stereochemical control of the internal Michael reaction. A new construction of trans-hydrindan systems
Nakatsubo et al. Synthetic studies toward mitomycins. 1. Total synthesis of deiminomitomycin A
Machlis et al. The structure of sirenin
Snider et al. Total synthesis of (.+-.)-nitramine. Development of a ketene equivalent in the ene reaction
Trost et al. Palladium-mediated cycloaddition approach to loganin aglucon
House et al. Perhydroindanone Derivatives. I. Applicability of the Diels-Alder Reaction
Hiyama et al. Regio-and stereoselective cyclopentannulation with ketones and propargyl alcohol derivatives. Synthesis of dl-nootkatone and dl-muscopyridine.
Trost et al. Methyl 2-pyridinesulfinate. A convenient reagent for sulfinylation-dehydrosulfinylation
Paquette et al. Synthetic studies relating to the structure of senoxydene. A sequential annulation approach to angular triquinane construction capable of varied tetramethyl substitution patterns
Hauser et al. Aklavin-type anthracyclinones: brief, regioispecific syntheses of tetracyclic intermediates
Marmsäter et al. Cyclic oxonium ylides: building blocks for iterative synthesis of polycyclic ethers
Kochhar et al. 3-Alkoxypyrroles by reduction of alkoxypyrrolinones
Marino et al. A regiospecific synthesis of functionalized vinylcyclopropanes via cyclopropyl cuprates
Paquette et al. Stereocontrolled access to the most highly condensed pentalenolactone antibiotic. From cycloheptatriene to pentalenolactone P methyl ester
de la Torre et al. Straightforward synthesis of the strong ambergris odorant γ-bicyclohomofarnesal and its endo-isomer from R-(+)-sclareolide
Jones et al. A short protocol for the synthesis of spirocyclic tetrahydrofurans via intramolecular O–H insertion
Broka et al. Synthetic studies on wortmannin and 11-desacetoxywortmannin
Roush et al. Improved synthesis of the perhydroindenone precursor of dendrobine
Martin et al. Carbonyl homologation with. alpha. substitution. A new synthesis of 4, 4-disubstituted 2-cyclopentenones
Tanimori et al. A new pathway to chiral tetracyclic indolidines via Pauson–Khand reaction
Suzuki et al. Tandem five membered-ring selective Prins reaction and Friedel–Crafts reaction
Lipa et al. Methano-bridged 10. pi.-electron aromatic annulenes. 4-Methoxy-1, 6-methanoisoquinoline
Muratake et al. Synthetic study of hetisine-type aconite alkaloids. Part 1: Preparation of tetracyclic intermediate containing the C14–C20 bond