Efficient Construction of Cyclopenta[<i>b</i>]quinoline Core of Isoschizozygane Alkaloids via Intramolecular Formal Hetero-Diels−Alder Reaction

Magomedov, Nabi A.

doi:10.1021/ol034776r

Cited by 41 publications

(13 citation statements)

References 15 publications

(5 reference statements)

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“…Similarly, cuspareine ( 2a ) and related compounds 2b and 2c have shown antibacterial as well as cytotoxic activity [24]. More complex systems include (+)-aspernomine ( 3 ), a potent cytotoxic agent [25] and (−)-isoschizogaline ( 4 ), a potentially useful antibiotic [26]. Finally, (−)-martinellic acid ( 5 ) is known to be a non-peptide antagonist for the bradykinin B 1 and B 2 receptors [27] (Figure 1).…”

Section: Survey Of New Methodologymentioning

confidence: 99%

Recent Syntheses of 1,2,3,4-Tetrahydroquinolines, 2,3-Dihydro-4(1H)-quinolinones and 4(1H)-Quinolinones using Domino Reactions

2013

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A review of the recent literature is given focusing on synthetic approaches to 1,2,3,4-tetrahydroquinolines, 2,3-dihydro-4(1H)-quinolinones and 4(1H)-quinolinones using domino reactions. These syntheses involve: (1) reduction or oxidation followed by cyclization; (2) S N Ar-terminated sequences; (3) acid-catalyzed ring closures or rearrangements; (4) high temperature cyclizations and (5) metal-promoted processes as well as several less thoroughly studied reactions. Each domino method is presented with a brief discussion of mechanism, scope, yields, simplicity and potential utility.

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Section: Survey Of New Methodologymentioning

confidence: 99%

Recent Syntheses of 1,2,3,4-Tetrahydroquinolines, 2,3-Dihydro-4(1H)-quinolinones and 4(1H)-Quinolinones using Domino Reactions

2013

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“…To date, one racemic total synthesis by Heathcock and two synthetic studies have been reported. [54][55][56][57][58] Chart 4 depicts our synthesis of isoschizogamine. Oxidation of exo-norborneol (48) and a subsequent reaction with trisyl hydrazide afforded hydrazone 49.…”

Section: Synthesis Of Isoschizogaminementioning

confidence: 99%

Synthesis of Natural Products with Polycyclic Systems

Yokoshima

2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Herein we present our unique strategies to synthesize natural products. To prepare mersicarpine, an atypical indole alkaloid, our procedure features an Eschenmoser-Tanabe fragmentation to synthesize an alkyne unit, a combination of a Sonogashira coupling and a gold(III) catalyzed cyclization to construct the indole skeleton, and a one-pot process to arrange the cyclic imine and the hemiaminal moieties. Additionally, we synthesized a frog poison, histrionicotoxin, via a chirality transfer from an allenylsilane to prepare a pseudosymmetrical dienyne, dienyne metathesis to produce an optically active bicyclo [5.4.0] system, and an asymmetric propargylation. To synthesize lyconadin A, a Lycopodium alkaloid, a combination of an azaPrins reaction and electrocyclic ring opening constructed the highly fused tetracyclic compound. The synthesis of isoschizogamine features a facile construction of the carbon framework through a Wagner-Meerwein rearrangement, a tandem metathesis, a stereoselective rhodium-mediated 1,4-addition of an arylboronic acid, and a ring-closing metathesis via a hemiaminal ether.

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“…Isoschizogamine, an alkaloid isolated in 1963 from Schizozygia caffaeoides, 1,2) is a unique hexacyclic compound in that a tetrahydroquinoline, a hexahydroquinolizine, a pyrrolidinone, and a cyclopentane rings are fused to one another to form the hexacyclic skeleton, containing a quaternary carbon and an aminal moiety. 3) These intriguing structural features have attracted the attention of synthetic chemists, and five total syntheses, [4][5][6][7][8] including ours, and several synthetic studies have been reported to date. [9][10][11][12][13] In 2012, we reported the total synthesis of (−)-isoschizogamine 5) (Chart 1).…”

Section: Introductionmentioning

confidence: 99%

Synthetic Studies of Isoschizogamine: Alternative Preparation of the Key Intermediate

Hayashi

Miura

Yokoshima

et al. 2019

CHEMICAL & PHARMACEUTICAL BULLETIN

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An alternative synthetic route toward a key intermediate in the total synthesis of isoschizogamine is described. The Claisen-Johnson rearrangement stereoselectively constructed a quaternary carbon. Trifluoroperacetic acid mediated the Baeyer-Villiger oxidation to form a bicyclic lactone. The Mukaiyama-Matsuo protocol converted the lactone into an α,β-unsaturated lactone, that was used as the substrate for the rhodium-mediated 1,4-addition of an arylboronic acid.

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Efficient Construction of Cyclopenta[b]quinoline Core of Isoschizozygane Alkaloids via Intramolecular Formal Hetero-Diels−Alder Reaction

Cited by 41 publications

References 15 publications

Recent Syntheses of 1,2,3,4-Tetrahydroquinolines, 2,3-Dihydro-4(1H)-quinolinones and 4(1H)-Quinolinones using Domino Reactions

Recent Syntheses of 1,2,3,4-Tetrahydroquinolines, 2,3-Dihydro-4(1H)-quinolinones and 4(1H)-Quinolinones using Domino Reactions

Synthesis of Natural Products with Polycyclic Systems

Synthetic Studies of Isoschizogamine: Alternative Preparation of the Key Intermediate

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