Indole Diterpene Synthetic Studies:  Development of a Second-Generation Synthetic Strategy for (+)-Nodulisporic Acids A and B

Smith, Amos B.; Kürti, László; Davulcu, Akin H.; Cho, Young Shin; Ohmoto, Kazuyuki

doi:10.1021/jo062423a

Cited by 41 publications

(16 citation statements)

References 43 publications

(47 reference statements)

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“…Data for Eisomer: 1 2-Iodocyclohex-2-en-1-one (7). [69] As olution of iodine (6.35 g, 25.0 mmol) in 4-MeTHP (26 mL) was added to as olution of cyclohex-2-en-1-one (18)( 970 mL, 10.1 mmol) and pyridine (2.8 mL, 35 mmol) in 4-MeTHP (14 mL) through ad ropping funnel over 1h. After 2h,t he solution was diluted with n-hexane (40 mL) and quenched by the addition of 1 m aqueous NaHCO 3 (20 mL 1-(4-(2-(Dimethylamino)ethoxy)phenyl)-1,2-diphenylbutan-1-ol (20).…”

Section: -Methyl-2-phenethoxytetrahydro-2h-pyran (4 A) Colorless Oimentioning

confidence: 99%

4‐Methyltetrahydropyran (4‐MeTHP): Application as an Organic Reaction Solvent

Kobayashi

Tamura

Yoshimoto

et al. 2019

Chemistry An Asian Journal

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4-Methyltetrahydropyran (4-MeTHP) is ah ydrophobic cyclic ether with potential for industrial applications. We herein report, for the first time, ac omprehensive study on the performance of 4-MeTHP as an organic reaction solvent. Its broad application to organic reactions includes radical, Grignard, Wittig, organometallic, halogen-metal exchange, reduction,o xidation, epoxidation, amidation, esterification, metathesis, and other miscellaneous organic reactions. This breadth suggests4 -MeTHP can serve as a substitute for conventional ethers and harmful halogenated solvents. However,4 -MeTHP was found incompatible with strong Lewis acids, and the CÀOb ond was readily cleaved by treatment with BBr 3 .M oreover,t he radical-based degradation pathwayso f4 -MeTHP, THP and 2-MeTHF were elucidated on the basis of GC-MS analyses. The data reported herein is anticipated to be useful for ab road range of synthetic chemists,e specially industrial process chemists, when selecting the reactions olvent with green chemistry perspectives.[a] Dr.Scheme1.Manufacturing process of 4-MeTHP. IPEA = isopentyl alcohol, MHP = 2-hydroxy-4-methyltetrahydropyran, MPD = 3-methylpentan-1,5-diol.

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Section: -Methyl-2-phenethoxytetrahydro-2h-pyran (4 A) Colorless Oimentioning

confidence: 99%

4‐Methyltetrahydropyran (4‐MeTHP): Application as an Organic Reaction Solvent

Kobayashi

Tamura

Yoshimoto

et al. 2019

Chemistry An Asian Journal

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“…[22] This type of Pd II -mediated indole ring formation from o-alkenyl aniline derivatives has sparsely been documented for preparing much simpler indole derivatives with no substituent at the 2-and 3positions of the indole nucleus, [23] and has never been applied to the total synthesis of complex natural products. [24][25][26] Finally, selective removal of the acetal protecting group with hydrochloric acid accompanied by concomitant migration of the C13ÀC14 double bond gave the conjugated enone 5.…”

mentioning

confidence: 99%

Total Synthesis of the Tremorgenic Indole Diterpene Paspalinine

Enomoto¹,

Morita²,

Kuwahara³

2012

Angew Chem Int Ed

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“…While work has been done on the total syntheses of herbindoles [ 11 ] and trikentrines [ 12 ], which contain angular cyclopenta[ g ]indole partial structures [ 13 – 29 ], there is only little known on the assembly of linear cyclopenta[ f ]indole systems. Both existing approaches rely on the anellation of the pyrrole part to indene-based starting materials [ 30 – 33 ].…”

Section: Introductionmentioning

confidence: 99%

Study on the synthesis of the cyclopenta[f]indole core of raputindole A

Marsch¹,

Kock²,

Lindel³

2016

Beilstein J. Org. Chem.

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SummaryThe raputindoles from the rutaceous tree Raputia simulans share a cyclopenta[f]indole partial structure the synthesis of which is subject of this investigation. An efficient route to a series of 1,5-di(indol-6-yl)pentenones was developed via Mo/Au-catalyzed Meyer–Schuster rearrangement of tertiary propargylic alcohol precursors. However, none of the enones underwent the desired Nazarov cyclization to a cyclopenta[f]indole. More suitable were 6-hydroxyallylated indolines which gave good yields of cyclopenta[f]indolines after treatment with SnCl4, as soon as sterically demanding β-cyclocitral adducts were reacted. Most successful were Pt(II) and Au(I)-catalyzed cyclizations of N-TIPS-protected indolin-6-yl-substituted propargylacetates which provided the hydrogenated tricyclic cyclopenta[f]indole core system in high yield.

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Indole Diterpene Synthetic Studies: Development of a Second-Generation Synthetic Strategy for (+)-Nodulisporic Acids A and B

Cited by 41 publications

References 43 publications

4‐Methyltetrahydropyran (4‐MeTHP): Application as an Organic Reaction Solvent

4‐Methyltetrahydropyran (4‐MeTHP): Application as an Organic Reaction Solvent

Total Synthesis of the Tremorgenic Indole Diterpene Paspalinine

Study on the synthesis of the cyclopenta[f]indole core of raputindole A

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