Lipase-catalyzed resolution of 5-acetoxy-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene. Application to the synthesis of (+)-(3R,4S)-cis-4-hydroxy-6-deoxyscytalone, a metabolite isolated from Colletotrichum acutatum

Jimenez‐Teja, Daniel; Daoubi, Mourad; Collado, Isidro G.; Hernández-Galán, Rosario

doi:10.1016/j.tet.2009.02.054

Cited by 11 publications

(3 citation statements)

References 18 publications

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“…Cathepsin B and SHP2 are targets for screening anti-tumor agents, and IMPDH and PTPlB are targets for screening immunosuppressive and anti-diabetic agents, respectively. Previous studies reported that 17 was a phytotoxic substance and an important melanin biosynthetic intermediate in fungi [23]. Moreover, 17 was found to be a SHP2 and PTPlB inhibitor.…”

Section: Resultsmentioning

confidence: 96%

Polyketides from a Marine-Derived Fungus Xylariaceae sp.

Nong

Zheng²,

Zhang

et al. 2013

Marine Drugs

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Eighteen polyketides (1–18) including six citrinin derivatives, two phenol derivatives, one cyclopentenone, two naphthol derivatives, and seven tetralone derivatives were isolated from the culture broth of a marine-derived fungal strain Xylariaceae sp. SCSGAF0086. Five of these compounds (1, 2, 8, 9, and 10) were new, and their structures were determined by spectroscopic methods. Compounds 4, 6, 7, and 17 showed enzyme-inhibitory activities towards several tested enzymes, and 6 and 7 showed strong antifouling activity against Bugula neritina larvae settlement. This is the first time that the antifouling and enzyme-inhibitory activities of these compounds has been reported.

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Section: Resultsmentioning

confidence: 96%

Polyketides from a Marine-Derived Fungus Xylariaceae sp.

Nong

Zheng²,

Zhang

et al. 2013

Marine Drugs

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“…Specific rotation was measured in CH 3 Cl and THF (589 nm, T = 20 °C, 10 mm × 100 mm) with a digital polarimeter. Preparations of substrates 1a , , 1b , 1c , , 1e , 1g , 1i , , and 1j were performed as reported in literature.…”

Section: Methodsmentioning

confidence: 99%

Metal-Free Asymmetric Synthesis of Indanes through Chiral Hypervalent Iodine(III)-Mediated Ring Contraction

Ahmad

Silva

2016

J. Org. Chem.

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The iodine(III)-mediated asymmetric oxidative rearrangement of 1,2-dihydronaphthalenes was investigated to prepare optically active 1-substituted indanes. The chiral hypervalent iodine species is generated in situ from a chiral aryl iodide, prepared in 94% yield in one step. This metal-free protocol was applied to different cyclic alkenes, substituted with oxygen, with nitrogen, or at position 1 with aryl or methyl. Indanes can be isolated as an acetal or alcohol in up to 78% ee.

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“…The acetylation of phenols 88j, 88k and 88c was accomplished with DMAP, Ac 2 O in Et 3 N as solvent, 27 leading to protected alkenes 138j, 138k and 138c in 96%, 85% and 80% yields, respectively ( 13 C NMR. 86,87 The presence of five additional aromatic hydrogens in 1 H NMR data confirms the coupling product 138s. In addition, 13 C NMR spectrum shows the presence of carbonyl carbon at 164.8 ppm for compound 138s (Figure 16).…”

Section: Preparation Of Acetyl and Benzoyl Protected Olefinic Substratesmentioning

confidence: 57%

Exploring the iodine(III)-mediated ring contraction: new substrates, novel conditions and asymmetric reactions

Ahmad¹

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This journey would not have been thinkable without the support of great number of people. I wish to express my devoted thanks to my late father and mother whose prayers and affection eventually enabled me to complete this task and materialize my dreams. It's beyond expression to acknowledge their sacrifices, efforts, guidance, support, encouragement and firm dedication. Words become meaningless when I look at them as icons of strength for being what I am today. Words always seem to shallow whenever it comes to my dearest and loving brothers and sisters. I owe special thanks to them for their incredible love, kind motivation, encouragement, moral and financial support and standing unflinchingly beside me throughout my study. I am greatly indebted to my advisor and mentor Prof. Luiz Fernando da Silva Jr. for his continuous support, patience and motivation during the course of study. His personal interest, valuable suggestions and constructive discussions enabled me to complete this work objectively and successfully. I appreciate his kind supervision, systematic guidance and efforts he put into train me in the scientific field. Having him one simply could not wish for a better supervisor. I offer my cordial and profound thanks to our lab technician Joaquim Luis Matheus (Joca) for keeping the lab in running condition and for his kind tolerance of my mistakes. His helping hands were always there for me whenever needed especially in documentation of visa renewal. It would take forever to list all the help I got from him. I extend my deepest gratitude to Prof. Leandro Helgueira de Andrade and his student Rodrigo S. Martins for his generous contribution towards kinetic resolution of primary alcohols. I feel great pleasure in expressing my ineffable thanks to Prof. Josef Wilhelm Baader and Cassius Vinicius Stevani for his guidance and cooperation during my teaching assistantship. Special thanks to all the faculty members, technical and non-technical staff and students of chemistry institute for being a source of inspiration and enlightenment. In addition, I am obliged to all the members of analytical center for doing all the analyses on time and contributed to thesis. I would also like to give full credit to all my school, college and university teachers who shaped me into who I am. A good support system and friendly environment is important for surviving and staying abroad. It has been a great privilege to be part of the Prof. Helena group. I am lucky to have two wonderful friends Iris and Eloisa (Elo) who formed the core of my research time in Helena group. Simple is that they are irreplaceable all weather friends and I couldn't have survived without their scientific and non-scientific help. I admire their positive outlook and ability to smile in any situation. Friends, like Aline, Paulo and Siguara, you will instantly love and never forget once you meet them. They have been there for me and given me the freedom to ask them for advice and opinions on lab related issues. Special thanks and acknowledgement are extended to...

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Lipase-catalyzed resolution of 5-acetoxy-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene. Application to the synthesis of (+)-(3R,4S)-cis-4-hydroxy-6-deoxyscytalone, a metabolite isolated from Colletotrichum acutatum

Cited by 11 publications

References 18 publications

Polyketides from a Marine-Derived Fungus Xylariaceae sp.

Polyketides from a Marine-Derived Fungus Xylariaceae sp.

Metal-Free Asymmetric Synthesis of Indanes through Chiral Hypervalent Iodine(III)-Mediated Ring Contraction

Exploring the iodine(III)-mediated ring contraction: new substrates, novel conditions and asymmetric reactions

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