ChemInform Abstract: New Rubrolides from the Ascidian Synoicum blochmanni.

Ortega, Marı́a J.; Zubı́a, Eva; Ocana, Jose M.; Naranjo, Santiago; Salvá, Javier

doi:10.1002/chin.200039220

ChemInform

2000

DOI: 10.1002/chin.200039220

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ChemInform Abstract: New Rubrolides from the Ascidian Synoicum blochmanni.

Marı́a J. Ortega

Eva Zubı́a

Jose M. Ocana

et al.

Abstract: New Rubrolides from the Ascidian Synoicum blochmanni. -Six new rubrolides, e.g. (I), and four related known compounds are isolated from S. blochmanni. Rubrolide M exhibits potent cytotoxic activity. -(ORTEGA, MARIA J.; ZUBIA, EVA; OCANA, JOSE M.; NARANJO

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2009

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“…By using this method, we developed an expeditious approach to the synthesis of rubrolide E, a naturally occurring butenolide derivative belonging to rubrolides, a family of biologically active marine ascidian metabolites isolated from tunicate Ritterella rubra 10 and Synoicum blochmanni. 11 Because of their antibiotic and cytotoxic activities, the synthesis of these compounds is a subject of great current interest. 12 We prepared rubrolide E as follows: the Knoevenagel condensation product 5 was obtained in 55% yield through a one-pot process by adding piperidine and 4-anisaldehyde to the crude mixture derived from the reaction of 1a with methyl 4-hydroxy-2butenoate; subsequent treatment of 5 with BBr 3 gave rubrolide E in 52% overall isolated yield (Scheme 4).…”

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confidence: 99%

Palladium-Catalyzed Reaction of Arenediazonium Tetrafluoroborates with Methyl 4-Hydroxy-2-butenoate: An Approach to 4-Aryl Butenolides and an Expeditious Synthesis of Rubrolide E

Cacchi

Fabrizi

Goggiamani

et al. 2009

Synlett

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The palladium-catalyzed reaction of arenediazonium tetrafluoroborates with methyl 4-hydroxy-2-butenoate in MeOH under mild conditions gives 4-arylbutenolides usually in good to high yields through a domino vinylic substitution/cyclization process. The reaction tolerates a variety of useful substituents including the whole range of halogen substituents, nitro, ether, cyano, keto, and ester groups and can be performed as a one-pot process generating the arenediazonium salt in situ. By using this method, the marine antibiotic rubrolide E has been synthesized via an expeditious and efficient sequential protocol that omits the isolation of the butenolide intermediate (two operative steps, 52% overall yield).Because of their availability from inexpensive anilines, higher reactivity, utilization under aerobic and phosphinefree conditions in the absence of added bases, arenediazonium salts are an attractive alternative to aryl halides or triflates in Heck reactions. 1,2-5 Most of the applications described have been based on the palladium-catalyzed reaction of arenediazonium salts with monosubstituted olefins. 2 A variety of cyclic olefinic systems have also been investigated. 3 Very little, however, has been done with acyclic disubstituted olefins. Acyclic 1,1-disubstituted olefins have been used to prepare a-benzyl-b-keto esters 4 and (E)-dimethyl 2-benzylidensuccinates, 3e the reactivity of acyclic b-substituted and a,b-disubstituted acrylates has been investigated by Correia et al., 3e and (E)-4,4,4-trifluoro-1-phenyl-2-buten-1-one has been converted into the corresponding a-arylated derivatives. 5Our interest in the palladium chemistry of arenediazonium salts 3n,6 prompted us to investigate whether their reaction with 1,2-disubstituted olefins bearing a nucleophile at one olefinic terminus and an electrophile at the other one might lead to the de novo construction of functionalized cyclic derivatives through a domino Heck reactioncyclization process. In particular, we decided to explore the palladium-catalyzed reaction of arenediazonium salts with readily available alkyl 4-hydroxy-2-butenoate 7 (2) to develop a new route to the 4-arylbutenolide [or 4-aryl-2(5H)-furanone] skeleton 3 (Scheme 1), a structural unit that characterizes a large number of biologically important compounds. 8 Herein we report the results of this study.We initiated our study by subjecting 2a (R = Et) to 2 equivalents of 4-methoxydiazobenzene tetrafluoroborate (1a), a model of electron-rich arenediazonium salts, in the presence of 5 mol% of Pd(OAc) 2 in EtOH at 40°C for 8 hours. The expected butenolide product 3a was isolated in 50% yield along with a 19% yield of the acyclic derivative 4a, most probably because of the low regioselectivity of the carbopalladation step under these conditions (Table 1, entry 1). The starting arenediazonium salt 1a was recovered in 14% yield. We then switched to the methyl ester 2b (R = Me) in MeOH and found that 3a could be isolated in a 63% yield after 5.5 hours and that a higher regioselectivity in the carbopal...

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confidence: 99%

Palladium-Catalyzed Reaction of Arenediazonium Tetrafluoroborates with Methyl 4-Hydroxy-2-butenoate: An Approach to 4-Aryl Butenolides and an Expeditious Synthesis of Rubrolide E

Cacchi

Fabrizi

Goggiamani

et al. 2009

Synlett

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ChemInform Abstract: New Rubrolides from the Ascidian Synoicum blochmanni.

Abstract: New Rubrolides from the Ascidian Synoicum blochmanni. -Six new rubrolides, e.g. (I), and four related known compounds are isolated from S. blochmanni. Rubrolide M exhibits potent cytotoxic activity. -(ORTEGA, MARIA J.; ZUBIA, EVA; OCANA, JOSE M.; NARANJO

Cited by 1 publication

References 1 publication

Palladium-Catalyzed Reaction of Arenediazonium Tetrafluoroborates with Methyl 4-Hydroxy-2-butenoate: An Approach to 4-Aryl Butenolides and an Expeditious Synthesis of Rubrolide E

Palladium-Catalyzed Reaction of Arenediazonium Tetrafluoroborates with Methyl 4-Hydroxy-2-butenoate: An Approach to 4-Aryl Butenolides and an Expeditious Synthesis of Rubrolide E

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