(+)-Sorangicin A: evolution of a viable synthetic strategy

Smith, Amos B.; Dong, Shuzhi; Fox, Richard J.; Brenneman, Jehrod B.; Vanecko, John A.; Maegawa, Tomohiro

doi:10.1016/j.tet.2011.09.035

Cited by 32 publications

(16 citation statements)

References 145 publications

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“…Diynyl alcohol 1 was prepared by the reaction of 1,4‐bis(trimethylsilyl)‐1,3‐butadiyne S1 first with MeLi in Et 2 O, followed by addition of the dicyclopropyl ketone. Compound 1 , purified by column chromatography, was obtained in 91 % yield (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

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Reactions of Ruthenium Complexes Containing Pentatetraenylidene Ligand

Tsai

Lin

Liu

2016

Chemistry An Asian Journal

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Two ruthenium acetylide complexes [Ru]-C≡C-C≡C-C(OR)(C H ) (2, R=H and 2 a, R=CH ; [Ru]=Cp(PPh ) Ru) each with two cyclopropyl rings were synthesized from TMS-C≡C-C≡C-C(OH)(C H ) (1; TMS=trimethylsilyl). Treatments of 2 and 2 a with allyl halide in the presence of KPF afforded the vinylidene complexes 3 and 3 a, respectively. When NH PF was used, instead of KPF , additional ring-opening reaction took place on one of the three-membered ring. Treatment of [Ru]Cl with 1,3-butadiyne (6), bearing an epoxide ring, afforded acetylide complex 7 with a furyl ring. Treatment of 2 a with Ph CPF presumably afforded pentatetraenylidene complex {[Ru]=C=C=C=C=C(C H ) }[PF ] (10), which was not isolated. Additions of various alcohols in a solution of 10 generated a number of disubstituted allenylidene complexes {[Ru]=C=C=C(OR)-C=C(C H ) }[PF ] (11). Treatment of 11 with K CO afforded the acetylide complex 12 bearing a carbonyl group, characterized by single X-ray diffraction analysis. Addition of a primary amine to 10 caused cleavage of the farthermost C=C bond and several allenylidene complexes {[Ru]=C=C=C(Me)(NHR)}[PF ] (18) were isolated.

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Section: Resultsmentioning

confidence: 99%

“…Elemental analysis and X‐ray diffraction studies were carried out at the Regional Center of Analytical Instrument located at the National Taiwan University. The ruthenium complex [Ru]Cl ([Ru]=Cp(PPh 3 ) 2 Ru) and organic compound 1,4‐bis(trimethylsilyl)‐1,3‐butadiyne S1 were prepared by following the method reported in the literatures.…”

Section: Methodsmentioning

confidence: 99%

Reactions of Ruthenium Complexes Containing Pentatetraenylidene Ligand

Tsai

Lin

Liu

2016

Chemistry An Asian Journal

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“…To set the 5-( S )-configuration with an axial alcohol, we planned to reduce tetrahydropyranone 11 with L-Selectride. 18 Treatment of 11 with L-Selectride in THF at −78 °C for 1 h afforded alcohol 16 in 81% yield. This was converted to bis-TBS ether 17 in 52% yield over three steps.…”

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confidence: 99%

“…An asymmetric synthesis of tetrahydroprane derivative 19 bearing 5-( S )-configuration is also shown in Scheme . To set the 5-( S )-configuration with an axial alcohol, we planned to reduce tetrahydropyranone 11 with L-Selectride . Treatment of 11 with L-Selectride in THF at −78 °C for 1 h afforded alcohol 16 in 81% yield.…”

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confidence: 99%

Total Synthesis of GEX1Q1, Assignment of C-5 Stereoconfiguration and Evaluation of Spliceosome Inhibitory Activity

Ghosh

Effenberger

et al. 2014

Org. Lett.

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An enantioselective total synthesis of GEX1Q1 has been accomplished in a convergent manner. The C-5 asymmetric center has now been assigned through synthesis. GEX1Q1 displayed slightly better spliceosome inhibitory activity over its C-5 epimer. The salient features of this synthesis include an asymmetric hetero-Diels–Alder reaction to construct the tetrahydropyran ring and a Suzuki cross-coupling to assemble the key segments.

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“…306 The isomerisation observed in the classic Yamaguchi reaction and its modifications (e.g., Yonemitsu's and Shiina's conditions) was proposed to be a consequence of a reversible nucleophilic aza-Michael-type addition of DMAP onto the activated acid intermediate. 307 Therefore, in the synthesis of sorangicin A, the modified Mukaiyama reagent 2-bromo-1-ethyl-pyridinium tetrafluoroborate 130, 308 which possesses a non-nucleophilic counterion, was tested for the lactonisation step (Scheme 3.27). It was anticipated that this could minimise the isomerisation of the trienoacid 438.…”

Section: 26) 306mentioning

confidence: 99%

Towards Synthesis of Simplified Analogues of Pateamine A

Xu¹

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<p>Pateamine A (22) is a natural product that was isolated from a marine sponge inhabiting the coast of New Zealand. It exhibits potent inhibition of protein synthesis and nonsense-mediated mRNA decay through binding with eIF4A isoforms. Due to the scarcity of pateamine A (22) in the natural source and the low yield of total synthesis of pateamine A, it is necessary to prepare structurally simplified analogues which would allow further research on structure-activity relationships (SAR) of pateamine A (22). Based on the structure-activity relationship studies reported by Romo and co-workers, a simplified triazole analogue 182 lacking methyl groups was synthesized by Hemi Cumming, a previous Ph.D. student who studied at Victoria University of Wellington. The antiproliferative activity of this analogue was found to be significantly lower than that of pateamine A, suggesting that the thiazole embedded within the molecule or the excised methyl groups are crucial for its potency. Therefore, to further explore the necessary features for its selective activity for eIF4A isoforms, new thiazole analogues 183 – 186 and triazole analogues (10S)-and (10R)-analogue 187 were targeted in this project. The preparation of the thiazole-containing macrocyclic core of analogues 183 and 184 was achieved. It features: (1) gold-catalysed thiazole formation through coupling between an alkyne fragment and a thioamide fragment; (2) preparation of the Z,E-dienoate moiety by base-induced ring-opening of a δ-substituted-α, β-unsaturated lactone; and (3) a modified Mukaiyama macrolactonisation. The synthesis of the triazole-containing macrocyclic core of (10S)-analogue 187 was completed. It features: (1) a copper-catalysed triazole formation through 1,3-dipolar cycloaddition between an alkyne fragment and an azide fragment; (2) preparation of the Z,E-dienoate moiety by base-induced ring-opening of δ-substituted-α, β-unsaturated lactone; and (3) a modified Mukaiyama macrolactonisation. Studies on the preparation of a side-chain fragment with suitable functionalities to allow coupling with the various macrocycles through olefination reactions were also conducted. The attachment of the side-chain fragment onto the macrocyclic cores for the synthesis of the targeted analogues 183 and 184 and (10S)-analogue 187 will be investigated in future work. These experimental results will inform the synthesis of new generation analogues to further study the key structures required for effective binding to the protein target eIF4A and selectivity between isoforms.</p>

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(+)-Sorangicin A: evolution of a viable synthetic strategy

Cited by 32 publications

References 145 publications

Reactions of Ruthenium Complexes Containing Pentatetraenylidene Ligand

Reactions of Ruthenium Complexes Containing Pentatetraenylidene Ligand

Total Synthesis of GEX1Q1, Assignment of C-5 Stereoconfiguration and Evaluation of Spliceosome Inhibitory Activity

Towards Synthesis of Simplified Analogues of Pateamine A

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