Total synthesis of the homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine.

Tsuda, Yoshisuke; Hosoi, Shinzo; Ohshima, T.; Kaneuchi, Satomi; Murata, Masami; Kiuchi, Fumiyuki; Toda, Jun; Sano, Takehiro

doi:10.1248/cpb.33.3574

Cited by 12 publications

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“…Substituted tetrahydropyrrolo[1,2-a]isoquinoline-2,3-diones of type 56 [12,17,23,52] and their benzannelated analogs 83 [16,27,60] react with triallylborane at the C (2) =O group with the formation of the corresponding unsaturated alcohols 84 and 85 [60] …”

Section: Allylboronation Reactionsmentioning

confidence: 99%

“…The reaction of the N-substituted amide 3 with one mole of oxalyl chloride leads to the product from dehydration and closure of the 1,3-dioxazine ring, i.e., the enamine 4, which is acylated by a second molecule of oxalyl chloride with the formation of a derivative of pyrrolo[2,1-b][1,3]oxazinetrione 5 [21]. + -During treatment with oxalyl chloride 1-chloromethyl-and 1-methyl-6,7-dimethoxy-3,4,6,7-tetrahydroisoquinolines 6 [14], the substituted tetrahydro derivatives 7 of isoquinolines (n = 1) [7, 9, 11, 17-19, 22, 23] and 5H-benzo[c]azepines (n = 2) [24][25][26][27], the cyclohexaannelated tetrahydroisoquinolines 8 [28] and the dihydroisoquinolines 9 [16], and tetrahydrofuro [3,2-c]pyridine [29] form the corresponding 2,3-dihydro-2,3-pyrrolediones annelated with the azaheterocycles on the [a] side with good yields (57-82% …”

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confidence: 99%

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Synthesis and chemical transformations of 2,3-dihydropyrrole-2,3-diones annelated on the [a] side by azaheterocycles. (Review)

Mashevskaya

Масливец

2006

Chem Heterocycl Compd

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Data on methods for the synthesis of 2,3-dihydro-2,3-pyrrolediones condensed with azaheterocycles on the [a] side are reviewed. Their reactions with nucleophilic reagents, allylboronation, reduction, and thermal transformations are discussed.The chemistry of 2,3-dihydro-2,3-pyrrolediones condensed with azaheterocycles on the [a] side first evolved in the seventies, when the application of 2,3-dihydro-2,3-pyrroledione derivatives as synthetic blocks for the construction of alkaloid molecules was first demonstrated [1][2][3][4][5][6][7].It should be mentioned that up to the beginning of the nineties these annelated dihydropyrrolediones were studied almost exclusively as subjects for photoreduction and photocyclization or as dienophiles in DielsAlder reactions (for the production of intermediate compounds in the synthesis of alkaloids). A large part of these papers belong to certain groups of investigators [1][2][3][4][5]. Single reports on reactions with nucleophilic reagents, allylboronation, reduction, and thermal transformations of 2,3-dihydro-2,3-pyrrolediones annelated with azaheterocycles on the [a] side have only begun to appear comparatively recently. This region of their chemical behavior has been studied little in spite of the fact that they exhibit high reactivity toward various nucleophiles (particularly with the presence of several electron-withdrawing substituents in the rings) and generate imidoylketenes during thermolysis.In the present review we examine publications existing up to March, 2002, on methods for the production of dihydropyrrolediones condensed with azaheterocycles and their chemical transformations. The review does not include data on the chemistry of isatins and their aza analogs, which were described in [8], or data on the cycloaddition of these pyrrolediones, which have been discussed before [1][2][3][4][5][6][7][9][10][11] and were reviewed in [11].

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Section: Allylboronation Reactionsmentioning

confidence: 99%

mentioning

confidence: 99%

Synthesis and chemical transformations of 2,3-dihydropyrrole-2,3-diones annelated on the [a] side by azaheterocycles. (Review)

Mashevskaya

Масливец

2006

Chem Heterocycl Compd

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“…6c,7c,d,8i As in our β - erythroidine synthesis, Still—Gennari olefination 12 of neopentyl aldehyde 13 gave the Z -enoate 4 (Scheme 3). However, initial attempts to effect the Heck cyclization of vinyl bromide 4 using the conditions (Pd(OAc) 2 , PPh 3 , K 2 CO 3 ) employed in our previous β -erythroidine synthesis, as well as several other protocols (e.g., Pd(OAc) 2 , P( o -tolyl) 3 ,K 2 CO 3 ; Pd(OAc) 2 , AsPh 3 , i PrNEt 2 ; Pd(OAc) 2 , dppp, Et 3 N; Pd(PPh 3 ) 4 , NaOAc), provided E - dienoate 13 in very low yield (< 5%) along with decomposition of the starting material.…”

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confidence: 91%

“…5f Although far fewer synthetic efforts towards the synthesis of the homo erythrinan alkaloids have been reported, Tsuda and coworkers reported the total synthesis of a number of aromatic homo erythrinan alkaloids, including comosine. 6 The nonaromatic homo erythrinans in contrast have been less explored and to date no viable approaches have been reported.…”

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Total synthesis of (±)-isophellibiline

Funk

Belmar

2012

Tetrahedron Letters

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The total synthesis of (±)-isophellibiline is described. This represents the first synthesis of a member of the nonaromatic homoerythrinan family of alkaloids. The tetracyclic ring system of the natural product was quickly assembled by a strategy that features a retrocycloaddition/cycloaddition reaction of an amidodioxin, an intramolecular Heck reaction and a 6π-electrocyclic ring closure of a dienoic acid.

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The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

Krapcho

Ciganek

2013

Organic Reactions

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The Krapcho reaction involves esters with α‐electron‐withdrawing substituents such as malonates, β‐keto esters, and α‐cyano esters, which undergo dealkoxycarbonylation on being heated in polar aprotic solvents (such as DMSO, DMF, or HMPT) in the presence of water, or in polar aprotic solvents with water in the presence of added salts (such as NaCN, NaCl, LiCl, LiI, or MgCl 2 ). This procedure avoids the use of strongly aqueous acidic and alkaline conditions and tolerates many functional and protecting groups. The chapter presents the mechanistic aspects of this procedure, which include reaction parameters such as solvents, salts, other additives, and the use of microwave irradiation. The diastereoselectivity of protonation of the enolate intermediate leading to the dealkoxycarbonylated products is discussed. Trapping of the intermediate enolate by electrophiles other than a proton is illustrated. Potential side reactions and same‐pot subsequent reactions of substrates are discussed along with functional‐group compatibility for halogens and nitrogen, oxygen, sulfur, selenium, and carbon functional groups. Several examples of applications of this methodology for the synthesis of natural products along with experimental conditions and procedures are presented. Closely related methods are discussed in the Comparison with Other Methods section. The tables, which consist of 371 pages, are grouped according to substrate structure. Selective entries for other methods (excluding classical aqueous acidic or basic methods) are included in the tabular survey for comparative purposes.

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Total synthesis of the homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine.

Cited by 12 publications

References 0 publications

Synthesis and chemical transformations of 2,3-dihydropyrrole-2,3-diones annelated on the [a] side by azaheterocycles. (Review)

Synthesis and chemical transformations of 2,3-dihydropyrrole-2,3-diones annelated on the [a] side by azaheterocycles. (Review)

Total synthesis of (±)-isophellibiline

The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

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