Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

• Emine Salamci and
• Ayse Kilic Lafzi

Beilstein J. Org. Chem. 2022, 18, 1539–1543, doi:10.3762/bjoc.18.163

• cyclitols [30][31][32][33] and C8-aminocyclitols [18][19][20][21][22][23][24], we were interested in developing an efficient synthesis of aziridinecyclooctanediol. In the present paper, we report the efficient synthesis of aziridinecyclooctanediol and a new 3-aminocyclooctanetriol stereoisomer starting from

Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols

• Emine Salamci and
• Yunus Zozik

Beilstein J. Org. Chem. 2021, 17, 705–710, doi:10.3762/bjoc.17.59

• stereospecifically new chlorocyclooctanetriols. Keywords: aminocyclitols; aminocyclooctanetriol; chlorocyclooctanetriol; cyclic sulfate; cyclitols; Introduction The synthesis of aminocyclitols has attracted attention because they contain substructures of many biologically active natural products [1][2][3]. They

• have become important structural components for drug development with a modifying action as inhibitors of glycosidases [4][5][6][7][8][9][10]. Aminocyclitols are amino polyhydroxy cycloalkanes [2] formally derived from cyclitols [11][12][13][14][15], which are polyhydroxylated cycloalkanes, via

• the development of the first synthesis of some C8-amino- and chloro-substituted cyclitols. Recently, we developed the first synthesis of various C8-amino- [29][31] and diaminocyclitol derivatives [30]. As part of our work involving the synthesis of C8-cyclitols, we report the stereospecific syntheses

Synthesis of polyhydroxylated decalins via two consecutive one-pot reactions: 1,4-addition/aldol reaction followed by RCM/syn-dihydroxylation

• Michał Malik and
• Sławomir Jarosz

Beilstein J. Org. Chem. 2016, 12, 2602–2608, doi:10.3762/bjoc.12.255

• to their similarity to carbohydrates, these compounds often possess interesting biological properties, e.g., they may act as glycosidase inhibitors [2][3][4]. One of such compounds, acarbose [5][6][7], found an application as a drug and is marketed worldwide. Five- and six-membered cyclitols are a

• well-known and recognizable group of carbasugars. The synthesis of these monocyclic compounds (such as 1 and 2, Figure 1) and evaluation of their biological properties remain a challenging and vital research area [8][9][10][11]. On the other hand, bicyclic analogs of cyclitols are not as well

Some aspects of radical chemistry in the assembly of complex molecular architectures

• Béatrice Quiclet-Sire and
• Samir Z. Zard

Beilstein J. Org. Chem. 2013, 9, 557–576, doi:10.3762/bjoc.9.61

• of β-elimination. This constitutes a tremendous synthetic asset and explains the popularity and importance of radical-based methods for the manipulation and modification of oxygen-rich compounds such as carbohydrates and cyclitols. It is, however, possible to transform an alcohol into a leaving group

Synthesis of a new class of aminocyclitol analogues with the conduramine D-2 configuration

• Latif Kelebekli,
• Yunus Kara and
• Murat Celik

Beilstein J. Org. Chem. 2010, 6, No. 15, doi:10.3762/bjoc.6.15

• KMnO4 or OsO4 followed by acetylation gave the acetate derivatives, the exact configuration of which was determined by spectroscopic methods. Hydrolysis of the oxazolidinone rings and removal of the acetate groups furnished the desired aminocyclitols. Keywords: aminocyclitol; cyclitols; endoperoxide

• diols in the presence of p-toluenesulfonyl isocyanate for the introduction of the amino alcohol functionality. We are currently interested in the synthesis of cyclitols and their derivatives [25]. As a part of our program directed towards the synthesis of potential glycosidase inhibitors we used a

Single and double stereoselective fluorination of (E)-allylsilanes

• Marcin Sawicki,
• Angela Kwok,
• Matthew Tredwell and
• Véronique Gouverneur

Beilstein J. Org. Chem. 2007, 3, No. 34, doi:10.1186/1860-5397-3-34

• fluorination to afford allylic fluorides with clean transposition of the double bond. Using chiral cyclic allylsilanes, these experiments have culminated in efficient methods for the asymmetric synthesis of monofluorinated cyclitols or vitamin D3 analogues. [12][13][14][15] The key step of these syntheses is a

Synthesis and glycosidase inhibitory activity of new hexa- substituted C8-glycomimetics

• Olivia Andriuzzi,
• Christine Gravier-Pelletier,
• Gildas Bertho,
• Thierry Prangé and
• Yves Le Merrer

Beilstein J. Org. Chem. 2005, 1, No. 12, doi:10.1186/1860-5397-1-12

• consisting of six-membered cyclitols, related to valiolamine, [14] voglibose, [15] valienamine, [16] and acarbose. [17] The last two compounds, marketed as Basen® and Glucor® or Precose®, respectively, are also actually used in the treatment of type 2 diabetes. All these compounds can have their amino moiety