Acetolysis of 4-homoadamantyl tosylate

Nordlander, J. Eric; Wu, Fan; Jindal, Satya P.; Hamilton, John

doi:10.1021/ja01042a057

Cited by 26 publications

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“…Condensation of 20 with phthalic anhydride in refluxing DMF gave the corresponding phthalimide 13 . The overall yield from 2‐adamantanone to phthalimide 13 was 62%, higher than previously published synthetic pathway via alcohol 21 (25,26) that was transformed to 13 in a Mitsunobu reaction with an overall yield of 35% (16).…”

Section: Resultsmentioning

confidence: 63%

Evaluation of Antiproliferative Effect of N‐(alkyladamantyl)phthalimides In vitro

et al. 2012

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A series of (1‐adamantyl)phthalimides, 1–4, and (2‐adamantyl)phthalimides, 5–8, characterized by different chain length between the adamantyl and the phthalimide moiety were synthesized, as well as 1‐ and 2‐adamantylphthalimides substituted by nitro 9, 10, and amino group 11, 12, and phthalimides bearing homoadamantyl 13 and protoadamantyl substituent 14 and 15. The compounds were tested for antiproliferative activity in vitro on a series of five human cancer lines: MCF‐7 (breast carcinoma), SW 620 (colon carcinoma), HCT 116 (colon carcinoma), MOLT‐4 (acute lymphoblastic leukemia), H 460 (lung carcinoma), and a non‐tumor cell line HaCaT (human keratinocytes). All compounds except nitro derivatives 9 and 10 exhibited antiproliferative activity. The activity was generally better in the 2‐adamantyl series 5–8 and in the compounds having the longest alkyl spacers as in 4 and 8, or with an amino group as in 9 and 10. The most active compounds with the propylene spacer 4 and 8 showed the highest selectivity toward tumor cells. The activity was found to be due to a delay in the progress through the cell cycle at G1/S phase.

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Section: Resultsmentioning

confidence: 63%

Evaluation of Antiproliferative Effect of N‐(alkyladamantyl)phthalimides In vitro

et al. 2012

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“…Homoadamantanone 3 was first reduced to the alcohol 4 [57–59] and subsequently converted to homoadamantyl phthalimide 5 in moderate yield via the Mitsunobu protocol [60] (Scheme 2). …”

Section: Resultsmentioning

confidence: 99%

Photoinduced homolytic C–H activation inN-(4-homoadamantyl)phthalimide

Cindro¹,

Horvat²,

Mlinarić‐Majerski³

et al. 2011

Beilstein J. Org. Chem.

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Summary N-(4-homoadamantyl)phthalimide (5) on excitation and population of the triplet excited state underwent intramolecular H-abstractions and gave products 6 and 7. The major product, exo-alcohol 6 was a result of the regioselective δ H-abstraction and the stereoselective cyclization of the 1,5-biradical. Minor products 7 were formed by photoinduced γ H-abstractions, followed by ring closure to azetidinols and ring enlargement to azepinediones. The observed selectivity to exo-alcohol 6 was explained by the conformation of 5 and the best orientation and the availability of the δ-H for the abstraction.

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“…Synthesis of tricyclo [5.3.1.1 3,9 ]dodecane (14) Tricyclo[5.3.1.1 3,9 ]dodecane (14) is known and has been synthesized by a twofold Tieffenau-Demjanov ring expansion of 2-adamantanone, producing first tricyclo[4.3.1.1 3,8 ]undecan-4-one (9) (homoadamantanone) 9 and then tricyclo[5.3.1.1 3,9 ]dodecan-4-one (12) (bishomoadamantanone) 10 in 48-85% and 15% yields respectively. Another method for the preparation of 9 makes use of a selective C-H insertion of dichlorocarbene into adamantane followed by a hydrolytic rearrangement 11 (63% yield).…”

Section: Resultsmentioning

confidence: 99%

“…The compounds tricyclo[4.3.1.1 3,8 ]undecan-4-one 11 (9), 2-ethyl-2-adamantan-2-ol 16 and tricyclo[5.3.1.1 3,9 ]dodec-3-ene 13 (18), were prepared according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

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Preparation of the tricyclo[5.3.1.1^3,9]dodeca‐1,5‐diyl dication: attempts to prepare a novel µ‐H cation

Taeschler

Parvez

Sorensen

2001

J of Physical Organic Chem

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The tricyclo[5.3.1.1 3,9 ]dodeca-3,7-diyl dication (6) was prepared in situ and characterized by 1 H and 13 C NMR spectroscopy. Reaction of this dication with isopentane, NaBH 4 or H 2 , in an attempt to prepare the m-H cation 7, did result in hydride transfer, but to the 'outside' face of the dication, leading to the conventional monocation 8, or rearrangement products of this. This monocation was independently prepared, and is thermally less stable than the dication, rearranging to the 2-ethyl-2-adamantyl cation (19) at À60°C, DG ‡ = 16.0 AE 0.6 kcal mol À1 . The 2methyltricyclo[4.3.1.1 3,7 ]undec-2-yl cation (20), a likely intermediate in this rearrangement, was also independently prepared and shown to rearrange to 19, DG ‡ = 14.4 AE 0.3 kcal mol À1 , consistent with a stepwise rearrangement process for 8→[20]→19. The structures of dication 6 and monocation 8 were investigated by high-level ab initio calculations, and modeling studies were carried out to look at the factors that allow dications such as 6 to even be prepared.

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Acetolysis of 4-homoadamantyl tosylate

Cited by 26 publications

References 0 publications

Evaluation of Antiproliferative Effect of N‐(alkyladamantyl)phthalimides In vitro

Evaluation of Antiproliferative Effect of N‐(alkyladamantyl)phthalimides In vitro

Photoinduced homolytic C–H activation inN-(4-homoadamantyl)phthalimide

Preparation of the tricyclo[5.3.1.1^3,9]dodeca‐1,5‐diyl dication: attempts to prepare a novel µ‐H cation

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Acetolysis of 4-homoadamantyl tosylate

Cited by 26 publications

References 0 publications

Evaluation of Antiproliferative Effect of N‐(alkyladamantyl)phthalimides In vitro

Evaluation of Antiproliferative Effect of N‐(alkyladamantyl)phthalimides In vitro

Photoinduced homolytic C–H activation inN-(4-homoadamantyl)phthalimide

Preparation of the tricyclo[5.3.1.13,9]dodeca‐1,5‐diyl dication: attempts to prepare a novel µ‐H cation

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Preparation of the tricyclo[5.3.1.1^3,9]dodeca‐1,5‐diyl dication: attempts to prepare a novel µ‐H cation