Preparation of an advanced intermediate for the synthesis of leustroducsins and phoslactomycins by heterocycloaddition

• Anaïs Rousseau,
• Guillaume Vincent and
• Cyrille Kouklovsky

Beilstein J. Org. Chem. 2022, 18, 1385–1395, doi:10.3762/bjoc.18.143

• studies for the conversion of enol phosphate to the corresponding ketone were accomplished using an unprotected primary alcohol. However, it appeared that hydroxy group protection was necessary: control experiments made on the racemic cycloadduct 8 showed that basic hydrolysis of the enol phosphate led to

Strategies for the synthesis of brevipolides

• Yudhi D. Kurniawan and
• A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

• (−)-DIPT affording ent-85 in 65% yield. A series of functional group transformations involving hydroxy group protection, reduction of the epoxide, protection of the resultant free alcohol as TBS ether, and removal of the acetal protection afforded the expected allylic alcohol 83. Accordingly, cross

Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: toward the emergence of new building blocks

• Clémence Moitessier,
• Ahmad Rifai,
• Pierre-Edouard Danjou,
• Isabelle Mallard and
• Francine Cazier-Dennin

Beilstein J. Org. Chem. 2019, 15, 721–726, doi:10.3762/bjoc.15.67

• ; hydroxy group protection; 4-hydroxy-ortho-phthalaldehyde; ortho-phthalaldehyde; oxidation; Introduction Benzene-1,2-dicarboxaldehyde, also called ortho-phthalaldehyde (OPA) was employed in different domains such as in analytical and organic chemistry. In fact, it is one of the most commonly used

Efficient syntheses of climate relevant isoprene nitrates and (1R,5S)-(−)-myrtenol nitrate

• Sean P. Bew,
• Glyn D. Hiatt-Gipson,
• Graham P. Mills and
• Claire E. Reeves

Beilstein J. Org. Chem. 2016, 12, 1081–1095, doi:10.3762/bjoc.12.103

• ’ starting material its reaction with vinylmagnesium bromide afforded racemic 3° allylic alcohol rac-68 in an 88% yield. Subsequent hydroxy group protection using tert-butyldimethylsilyl chloride and imidazole afforded orthogonally protected O-TBDMS/PMB ether rac-69 in a moderate 53% yield. Needless to say

Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?

• Tobias-Elias Gloe,
• Insa Stamer,
• Cornelia Hojnik,
• Tanja M. Wrodnigg and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2015, 11, 1096–1104, doi:10.3762/bjoc.11.123

• (C-glycosyl-type pentose analogues) without the need of hydroxy group protection (Scheme 1). For a long time this reaction has been judged as unsuitable for preparative use as it typically leads to a complex mixture of products accompanied with a low yield of the rearrangement product itself [1

Synthesis of multivalent carbohydrate mimetics with aminopolyol end groups and their evaluation as L-selectin inhibitors

• Joana Salta,
• Jens Dernedde and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2015, 11, 638–646, doi:10.3762/bjoc.11.72

• of aminopyran 1 or serinol (2) and their evaluation as selectin inhibitors. Hydroxy group protection of aminopyran 1 to give compound 3, synthesis of amide 4 and subsequent deprotection. Conditions: a) TBSOTf, Et3N, DMAP, DMF, 5 d, 0 °C to rt; b) hexanoyl chloride, Et3N, CH2Cl2, 18 h, rt; c) HF