New approaches toward the synthesis of (D-homo) steroid skeletons using Mukaiyama reactions

Sarabèr, Florence C.E.; Baranovsky, A. V.; Jansen, B. J. M.; Posthumus, M.A.; Groot, Aede de

doi:10.1016/j.tet.2005.11.056

Cited by 21 publications

(12 citation statements)

References 52 publications

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“…Our approach to the synthesis of 5 began with a novel stereoselective approach to the C1-C9 fragment as shown in Scheme 2. The Mukaiyama aldol reaction 18 between the 2,2-disubstituted silylenolether 13 (obtained by a regioselective silylation of 2-methylcyclohexanone) 19 and 3-trimethylsilylpropynal provided the corresponding racemic aldol product (syn:anti 10 : 90) from which the pure anti isomer (AE)-14 was isolated in 60% overall yield. 20 It is worth noting that BF 3 $OEt 2 afforded a cleaner reaction with better anti stereoselectivity among the Lewis acids that we explored: i.e.…”

Section: Chemistrymentioning

confidence: 99%

Design, synthesis and initial biological evaluation of a novel pladienolide analog scaffold

et al. 2011

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A novel and simplified synthetic scaffold based on pladienolide was designed using a consensus pharmacophore hypothesis. An initial target was synthesized and evaluated to examine the role of the 3-hydroxy group and the methyl groups present at positions 10, 16, 20, 22 in 1, on biological activity. We report the first totally synthetic analog of this macrolide that shows biological activity. Our novel synthetic strategy enables the rapid synthesis of other new analogs of pladienolide in order to develop selective anticancer lead compounds.

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Section: Chemistrymentioning

confidence: 99%

Design, synthesis and initial biological evaluation of a novel pladienolide analog scaffold

et al. 2011

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“…In another application, 6-methoxytetralone has been utilized as a substrate for the construction of steroids [18]. It is noteworthy that 2-(1H-pyrazol-1-yl)-thiazole derivatives, which possess a conformationally constrained scaffold, similar to the one envisaged in this work, exhibited a potent EP1 receptor antagonist profile [19].…”

Section: Introductionmentioning

confidence: 79%

Novel conformationally constrained pyrazole derivatives as potential anti-cancer agents

Kasiotis

Tzanetou

Stagos

et al. 2015

Zeitschrift Für Naturforschung B

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The synthesis of 17 novel conformationally constrained pyrazole derivatives is reported herein, along with the assessment of their anti-proliferative and antiangiogenic activities. The evaluation of their inhibitory effect on cell proliferation against HepG2, HeLa, and MCF-7 cells revealed the pyrrolo[2,3-g]indazole 23 as a potent inhibitor of cell growth with IC 50 values of 5 μm. Additionally, the inhibition of vascular endothelial growth factor by pyrazoles 20 and 23 (30 % and 35 %, respectively) in HeLa supernatant cells was evidenced. These findings highlight the usefulness of these compounds as potential scaffolds for the design and development of novel anticancer agents with pronounced anti-angiogenic activity.

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“…To a solution of nitrosobenzene (10.80 g, 100.7 mmol) in CH 2 Cl 2 (210 mL) was added acetic acid (5.76 mL, 100 mmol) and (5-isopropenyl-2-methyl-cyclohexa-1,3-dienyloxy)-trimethylsilane 43 (9.33 g, 42.0 mmol) at -78 °C. The solution was stirred at this temperature for 12 h before being warmed to room temperature and further stirred for 4 h. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (silica gel, ethyl acetate/petroleum ether, 1/2) to provide 13 (4.12 g, 59%) as yellow oil.…”

Section: Methodsmentioning

confidence: 99%

Total synthesis and structure–activity relationship study of the potent cAMP signaling agonist (−)-alotaketal A

et al. 2013

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A detailed account of the first total synthesis of alotaketal A, a tricyclic spiroketal sesterterpenoid that potently activates the cAMP signaling pathway, is provided. The synthesis employs both intra- and intermolecular reductive allylation of esters for assembling one of the fragments and their coupling. A Hg(OAc)2-mediated allylic mercuration is used to introduce the C22-hydroxyl group. The subtle influence of substituents over the course of the spiroketalization process is revealed. The synthesis confirms the relative and absolute stereochemistry of (-)-alotaketal A and allows verification of alotaketal A’s effect over cAMP signaling using reporter-based FRET imaging assays with HEK 293T cells. Our studies also revealed alotaketal A’s unique activity in selectively targeting nuclear PKA signaling in living cells.

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New approaches toward the synthesis of (D-homo) steroid skeletons using Mukaiyama reactions

Cited by 21 publications

References 52 publications

Design, synthesis and initial biological evaluation of a novel pladienolide analog scaffold

Design, synthesis and initial biological evaluation of a novel pladienolide analog scaffold

Novel conformationally constrained pyrazole derivatives as potential anti-cancer agents

Total synthesis and structure–activity relationship study of the potent cAMP signaling agonist (−)-alotaketal A

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