LiCl-mediated, easy, and low-cost removal of the trityl group from protected alcohols and diols

Behloul, Cherif; Chouti, Aicha; Chabour, Ihssene; Bey, Hind Bengliz; Guijarro, David; Foubelo, Francisco; Nájera, Carmén; Yus, Miguel

doi:10.1016/j.tetlet.2016.06.110

Cited by 4 publications

(1 citation statement)

References 27 publications

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“…The next step involved the selective removal of the trityl group so as to facilitate the synthesis of the two separate C 5 fragments which would be coupled to yield the desired product. Unfortunately, the anticipated selective removal of the trityl group in the presence of an N-benzyl group did not yield the desired product [22][23][24][25][26]. Several selective trityl deprotection attempts gave different results: either the reaction did not proceed at all yielding starting material, or both the trityl and benzyl group were removed or all three protecting groups were removed.…”

Section: Resultsmentioning

confidence: 99%

Total synthesis of ent-pavettamine

Zimuwandeyi¹,

Fernandes²,

Rousseau³

et al. 2021

Beilstein J. Org. Chem.

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Pavettamine, a plant toxin first isolated from Pavetta harborii in 1995, was previously identified as a polyamine with C2 symmetry and a 1,3-syn-diol moiety on a C10 carbon backbone – one of very few substituted polyamines to be isolated from nature. Its absolute configuration was later established by our first reported total synthesis in 2010. Herein we report the first total synthesis of the enantiomer of pavettamine, ent-pavettamine. The symmetrical structure of the molecule allows for the synthesis of a common C5 fragment that can be divergently transformed into two synthons for later convergent coupling to furnish the target carbon framework. Based on the success of the protocol we employed for the synthesis of the naturally occurring pavettamine, (S)-malic acid was again the starting material of choice for the synthesis of the two individual C5 fragments, with strategic differences in terminal-group manipulation allowing for the synthesis of ent-pavettamine rather than pavettamine. Chain extension and stereoselective ketone reduction were achieved using the (R)-methyl p-tolyl sulfoxide chiral auxiliary to give the desired 1,3-syn-diol C5 unit. A protecting-group strategy was also developed for the orthogonal protection of the alcohol and amine functional groups as they were unveiled. The functionalized C5 fragments were coupled via reductive amination revealing the C10 carbon backbone. Deprotection of the alcohol and amine functional groups successfully provided ent-pavettamine as a TFA salt.

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Section: Resultsmentioning

confidence: 99%

Total synthesis of ent-pavettamine

Zimuwandeyi¹,

Fernandes²,

Rousseau³

et al. 2021

Beilstein J. Org. Chem.

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ChemInform Abstract: LiCl‐Mediated, Easy, and Low‐Cost Removal of the Trityl Group from Protected Alcohols and Diols.

et al. 2016

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Indium-mediated cleavage of the trityl group from protected alcohols and diols

et al. 2016

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The reaction of primary, secondary, allylic and benzylic trityl ethers with indium powder in MeOH/NH 4 Cl led to reductive cleavage of the trityl-oxygen bond, affording the corresponding alcohols in good to excellent yield under very mild reaction conditions. The detritylation process could successfully be extended to mono and detritylated diols. This methodology represents a new and efficient detritylation procedure under mild reaction conditions.

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LiCl-mediated, easy, and low-cost removal of the trityl group from protected alcohols and diols

Abstract: M., LiCl-mediated, easy and low-cost removal of the trityl group from protected alcohols and diols, Tetrahedron Letters (2016), doi: http://dx.

Cited by 4 publications

References 27 publications

Total synthesis of ent-pavettamine

Total synthesis of ent-pavettamine

ChemInform Abstract: LiCl‐Mediated, Easy, and Low‐Cost Removal of the Trityl Group from Protected Alcohols and Diols.

Indium-mediated cleavage of the trityl group from protected alcohols and diols

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