Synthesis of 1,4-dideoxy-1,4-imino-derivatives of d-allitol, l-allitol and d-talitol: a stereo selective approach for azasugars

Chandrasekhar, B.; Madhan, A.; Rao, B. Venkateswara

doi:10.1016/j.tet.2007.06.044

Cited by 40 publications

(3 citation statements)

References 32 publications

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“…In this case, an α-amino aldehyde, prepared by addition of a 1,3-dithiane to a chiral N -sulfinyl imine, was used as the chiral starting material [ 56 ]. Syntheses of 1,4-dideoxy-1,4-imino derivatives of L-allitol and D-talitol were also accomplished following a similar RCM methodology by Rao and co-workers [ 57 ].…”

Section: Reviewmentioning

confidence: 99%

Metathesis access to monocyclic iminocyclitol-based therapeutic agents

Drăguţan¹,

Drăguţan²,

Mitan³

et al. 2011

Beilstein J. Org. Chem.

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SummaryBy focusing on recent developments on natural and non-natural azasugars (iminocyclitols), this review bolsters the case for the role of olefin metathesis reactions (RCM, CM) as key transformations in the multistep syntheses of pyrrolidine-, piperidine- and azepane-based iminocyclitols, as important therapeutic agents against a range of common diseases and as tools for studying metabolic disorders. Considerable improvements brought about by introduction of one or more metathesis steps are outlined, with emphasis on the exquisite steric control and atom-economical outcome of the overall process. The comparative performance of several established metathesis catalysts is also highlighted.

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Section: Reviewmentioning

confidence: 99%

Metathesis access to monocyclic iminocyclitol-based therapeutic agents

Drăguţan¹,

Drăguţan²,

Mitan³

et al. 2011

Beilstein J. Org. Chem.

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“…For the recent syntheses of 1,4-dideoxy-1,4-imino--allitol and 1,4-dideoxy-1,4-imino--ribitol, [72] the diene was prepared via the regioselective C-3 ring opening of enantiomerically pure 2,3-epoxypent-4-en-1-ol by allylamine, while the first asymmetric synthesis of 1,4-dideoxy-1,4-imino--talitol was achieved via the addition of vinylmagnesium bromide to a protected (S)-glyceraldimine derivative prior to RCM and dihydroxylation. [73] Rao and co-workers [74] also used a Grignard addition to prepare the diene of desired stereochemistry for the synthesis of 1,4-dideoxy-1,4-imino--allitol (139) (Scheme 26).…”

Section: Ring-closing Metathesismentioning

confidence: 99%

Recent Developments in the Synthesis of Pyrrolidine‐Containing Iminosugars

et al. 2010

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As noted inhibitors of glycosidases, iminosugars have enormous therapeutic potential in the treatment of a number of diseases such as cancer, diabetes, and lysosomal storage disorders. Accordingly, much effort has been expended over the past decades in developing novel and efficient methodologies for the synthesis of iminosugars. This microreview highlights recent (post 2005) developments in the synthesis of pyrrolidine‐containing iminosugars and includes discussions of methodologies such as ring‐closing metathesis, aldol and pericyclic reactions, and protecting‐group free strategies.

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“…The polyhydroxylated piperidines and pyrrolidines exhibit a strong inhibiting activity with respect to glycosidases and glycosyltransferases [46,47], they have underlain the preparation of anti-Aids drugs. Compounds of these groups show the antitumor, antidiabetes, antibacterial, and antiviral action [47][48][49][50]. The advances in the chemistry of saturated fi ve-and six-membered azaheterocycles were described in recent reviews [51][52][53][54][55].…”

Section: Introductionmentioning

confidence: 99%