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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 16
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Original Articles

Stereoselective Synthesis of (−)-Cytoxazone and (+)-5-Epi-cytoxazone

A. Ravi Kumar Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, India
,
G. Bhaskar Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, India
,
A. Madhan Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, India
&
B. Venkateswara Rao Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, IndiaCorrespondence[email protected]
Pages 2907-2916 | Received 25 Oct 2002, Published online: 19 Aug 2006

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Read on this site (2)

G. Smitha & C. Sanjeeva Reddy. (2006) Asymmetric Synthesis of (+)‐epi‐Cytoxazone. Synthetic Communications 36:12, pages 1795-1800.
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Zorana Tokic‐Vujosevic, Goran Petrovic, Bojana Rakic, Radomir Matovic & Radomir N. Saicic. (2005) Synthesis of (−)‐Cytoxazone and (+)‐epi‐Cytoxazone: The Chiral Pool Approach. Synthetic Communications 35:3, pages 435-447.
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Articles from other publishers (22)

Rekha, Sonam Sharma, Gurdeep Singh & Ramasamy Vijaya Anand. (2021) Tropylium Salt-Promoted Vinylogous Aza-Michael Addition of Carbamates to para- Quinone Methides: Elaboration to Diastereomerically Pure α,α′-Diarylmethyl Carbamates . ACS Organic & Inorganic Au 2:2, pages 186-196.
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Izabel Luzia Miranda, Pedro Henrique Costa Santos, Markus Kohlhoff, Gislaine Aparecida Purgato, Marisa Alves Nogueira Diaz & Gaspar Diaz‐Muñoz. (2021) Stereoselective synthesis of (−)‐cytoxazone and its unnatural congener (+)‐5‐ epi ‐cytoxazone . Chirality 33:8, pages 479-489.
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Macha Lingamurthy, Gopalal Rao Nalliboina, Maddimsetti Venkateswara Rao, Batchu Venkateswara Rao, Bonam Srinivasa Reddy & Halmuthur Mahabalarao Sampath Kumar. (2017) DDQ mediated stereoselective intermolecular benzylic CN bond formation: Synthesis of (−)-cytoxazone, (−)-4-epi-cytoxazone and their analogues and immunological evaluation of their cytokine modulating activity. Tetrahedron 73:11, pages 1473-1481.
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Izabel Miranda, Ítala Lopes, Marisa Diaz & Gaspar Diaz. (2016) Synthesis Approaches to (−)-Cytoxazone, a Novel Cytokine Modulator, and Related Structures. Molecules 21:9, pages 1176.
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Annavareddi Naresh, Maddimsetti Venkateswara Rao, Sudha Sravanti Kotapalli, Ramesh Ummanni & Batchu Venkateswara Rao. (2014) Oxazolidinone derivatives: Cytoxazone–Linezolid hybrids induces apoptosis and senescence in DU145 prostate cancer cells. European Journal of Medicinal Chemistry 80, pages 295-307.
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Catherine N. Slattery, Sarah O’Keeffe & Anita R. Maguire. (2013) Electronic effects of aryl-substituted bis(oxazoline) ligands on the outcome of asymmetric copper-catalysed C–H insertion and aromatic addition reactions. Tetrahedron: Asymmetry 24:20, pages 1265-1275.
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Chen-ming Hu, Lian-you Zheng, Ya-zhong Pei & Xu Bai. (2013) Synthesis of novel 3-aryl isoindolinone derivatives. Chemical Research in Chinese Universities 29:3, pages 487-494.
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Maria D. Rozwadowska & Anna Tomczak. (2009) The synthesis of (4S,5S)-(−)-isocytoxazone. Tetrahedron: Asymmetry 20:17, pages 2048-2051.
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K. C. Kumara Swamy, N. N. Bhuvan Kumar, E. Balaraman & K. V. P. Pavan Kumar. (2009) Mitsunobu and Related Reactions: Advances and Applications. Chemical Reviews 109:6, pages 2551-2651.
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Guillaume Bégis, David E. Cladingboel, Laure Jerome, William B. Motherwell & Tom D. Sheppard. (2009) Asymmetric Synthesis of Aminocyclopropanes and N -Cyclopropylamino Alcohols Through Direct Amidocyclopropanation of Alkenes Using Chiral Organozinc Carbenoids . European Journal of Organic Chemistry 2009:10, pages 1532-1548.
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Agnieszka Grajewska & Maria D. Rozwadowska. (2007) Stereoselective synthesis of cytoxazone and its analogues. Tetrahedron: Asymmetry 18:7, pages 803-813.
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Shyla George, Srinivasarao V. Narina & Arumugam Sudalai. (2007) NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity: a short route to (−)-cytoxazone and droxidopa. Tetrahedron Letters 48:8, pages 1375-1378.
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Srinivasarao V. Narina, Talluri Siva Kumar, Shyla George & Arumugam Sudalai. (2007) Enantioselective synthesis of (−)-cytoxazone and (+)-epi-cytoxazone via Rh-catalyzed diastereoselective oxidative C–H aminations. Tetrahedron Letters 48:1, pages 65-68.
Crossref
Maria D. Rozwadowska. (2006) Transformation of (+)-thiomicamine into the p-methylthio analogue of (+)-5-epi-cytoxazone. Tetrahedron: Asymmetry 17:11, pages 1749-1753.
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Abhimanyu S. Paraskar & Arumugam Sudalai. (2006) Enantioselective synthesis of (−)-cytoxazone and (+)-epi-cytoxazone, novel cytokine modulators via Sharpless asymmetric epoxidation and l-proline catalyzed Mannich reaction. Tetrahedron 62:24, pages 5756-5762.
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Ji Duck Kim, In Su Kim, Cheng Hua Jin, Ok Pyo Zee & Young Hoon Jung. (2005) Regioselective and Diastereoselective Amination with Use of Chlorosulfonyl Isocyanate:  A Short and Efficient Synthesis of (−)-Cytoxazone. Organic Letters 7:18, pages 4025-4028.
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Egidio Giorgio, Marin Roje, Katsunori Tanaka, Zdenko Hamersak, Vitomir Sunjic, Koji Nakanishi, Carlo Rosini & Nina Berova. (2005) Determination of the Absolute Configuration of Flexible Molecules by ab Initio ORD Calculations:  A Case Study with Cytoxazones and Isocytoxazones . The Journal of Organic Chemistry 70:17, pages 6557-6563.
Crossref
Okiko Miyata, Jun Hashimoto, Ryuuichi Iba & Takeaki Naito. (2005) Preparation of optically active α-hydroxy oxime ether by diastereoselective imino 1,2-Wittig rearrangement of hydroximates and its application to synthesis of (+)-cytoxazone. Tetrahedron Letters 46:23, pages 4015-4018.
Crossref
Zhong Jin. (2005) Muscarine, imidazole, oxazole and thiazole alkaloids. Natural Product Reports 22:2, pages 196.
Crossref
A. Madhan & B. Venkateswara Rao. (2005) Stereoselective synthesis of (3R,4S)-3-methoxy-4-methylaminopyrrolidine. Tetrahedron Letters 46:2, pages 323-324.
Crossref
Selena Milicevic, Radomir Matovic & Radomir N. Saicic. (2004) Stereoselective synthesis of (−)-cytoxazone and (+)-epi-cytoxazone. Tetrahedron Letters 45:5, pages 955-957.
Crossref
A. Ravi Kumar, G. Bhaskar, A. Madhan & B. Venkateswara Rao. (2003) Stereoselective Synthesis of (‐)‐Cytoxazone and (+)‐5‐Epi‐cytoxazone.. ChemInform 34:50.
Crossref

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