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M. Rahman, Ashanul Haque, J. Yadav (2020)
Stereoselective total synthesis of (−)-galantinic acid and 1-deoxy-5-hydroxysphingolipids via prins cyclizationTetrahedron Letters, 61
J. Yadav, P. Reddy, Hissana Ather, Alleni Kumar, A. Prasad, B. Reddy, Ahmad Khazim (2012)
Stereoselective Synthesis of (4S,6S)-6-Hydroxy-4-undecanolide: A Pheromone of the Giant White Butterfly Idea leuconoeSynthesis, 44
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Revised manuscript received: April 22, 2022 Version of record online: May 9, 2022 P e r s o n a l A c c o u n t
J. Yadav, M. Reddy, A. Prasad (2006)
Stereoselective syntheses of (−)-tetrahydrolipstatin via Prins cyclisationsTetrahedron Letters, 47
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J. Yadav, P. Rao, M. Reddy, A. Prasad (2008)
Stereoselective synthesis of basiliskamides A and B via Prins cyclisationTetrahedron Letters, 49
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G. Sabitha, Narjis Fatima, Peddabuddi Gopal, C. Reddy, J. Yadav (2009)
Stereoselective total synthesis of (+)-strictifolione and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one by Prins reaction and olefin cross-metathesisTetrahedron-asymmetry, 20
P. Reddy, A. Reddy, J. Yadav, B. Reddy (2012)
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Synthesis of natural products containing cyclohexane units utilizing the Ferrier carbocyclization reaction.Chemical record, 14 4
G. Sabitha, K. Reddy, G. Reddy, Narjis Fatima, J. Yadav (2005)
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Focused Update on the Prins Reaction and the Prins CyclizationChemInform, 43
J. Yadav, Hissana Ather, Uma Kamakolanu, N. Rao, A. Prasad (2008)
Stereoselective Formal Synthesisof Herbarumin III via Prins CyclizationSynthesis, 2008
Version of record online
G. Sabitha, M. Prasad, K. Shankaraiah, N. Reddy, J. Yadav (2010)
Convergent Synthesis of PassifloricinA via a Prins Cyclisation and Olefin Cross-Metathesis ApproachSynthesis, 2010
J. Yadav, N. Thrimurtulu, M. Venkatesh, K. Rao, A. Prasad, B. Reddy (2010)
Stereoselective Synthesis of(10S,12S)-10-Hydroxy-12-methyl-1-oxacyclo-dodecane-2,5-dionevia Prins CyclizationSynthesis, 2010
J. Yadav, P. Rao, M. Reddy, N. Rao, A. Prasad (2007)
Stereoselective synthesis of (+)-cryptocarya diacetate by an iterative Prins cyclisation and reductive cleavage sequenceTetrahedron Letters, 48
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Stereoselective Synthesis of(-)-PF1163A via Prins CyclizationSynlett, 2010
J. Yadav, B. Padmavani, B. Reddy, Ch. Venugopal, A. Rao (2007)
Total synthesis of diospongin A via an enzymatic kinetic resolution of (±)-tetrahydropyranol derived from Prins cyclizationSynlett, 2007
J. Yadav, M. Rahman, N. Reddy, A. Prasad (2015)
Synthesis of spiroketal fragment of ossamycin via Prins cyclizationTetrahedron Letters, 56
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Stereoselective Total Synthesis of Obolactone via Prins CyclizationSynthesis, 2010
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A convergent route to β-hydroxy δ-lactones through Prins cyclisation as the key step: synthesis of (+)-prelactones B, C and VTetrahedron Letters, 46
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Krishnaji Tadiparthi, P. Anand (2021)
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J. Yadav, B. Reddy, M. Reddy, Namelikonda Niranjan, A. Prasad (2003)
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Recent Advances in Prins SpirocyclizationEuropean Journal of Organic Chemistry, 2017
B. Reddy, P. Nair, Aneesh Antony, C. Lalli, R. Grée (2017)
The Aza‐Prins Reaction in the Synthesis of Natural Products and AnaloguesEuropean Journal of Organic Chemistry, 2017
J. Yadav, N. Kumar, M. Reddy, A. Prasad (2007)
Stereoselective synthesis of tarchonanthuslactone via the Prins cyclisationTetrahedron, 63
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Krishnaji Tadiparthi, P. Anand (2021)
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J. Yadav, M. Rahman, N. Reddy, A. Prasad, Ahmad Ghamdi (2014)
Stereoselective Total Synthesis of Rhoiptelol B via Prins CyclizationSynlett, 25
Yun Zhang, Jianxian Gong, Zhen Yang (2014)
Efficient total synthesis of bioactive natural products: a personal record.Chemical record, 14 4
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Asha Budakoti, P. Mondal, Prachi Verma, Jagadish Khamrai (2021)
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A. Frontier, Shukree Abdul-Rashed, Connor Holt (2020)
Alkynyl Prins and Alkynyl Aza-Prins Annulations: Scope and Synthetic ApplicationsSynthesis, 52
G. Sabitha, Narjis Fatima, E. Reddy, J. Yadav (2008)
Prins and RCM protocols for the synthesis of the pheromones of the giant white butterfly Idea leuconoeTetrahedron Letters, 49
The natural products having tetrahydropyran unit with multiple chiral centers serve as magnificent building blocks for various active pharmaceutical ingredients (APIs). ‘Prins cyclization is one of the wonderful strategies to construct tetrahydropyran unit stereoselectively in asymmetric synthesis. In this account, we discuss our research efforts toward the synthesis of various natural products from the past two decades (2005–2020) by using Prins cyclization as a key step. Further, the synthetic utility of this reaction was investigated and well demonstrated on various molecules successfully.
The Chemical Record – Wiley
Published: Aug 1, 2022
Keywords: Total synthesis; Natural products; Prins reaction; Tetrahyropyran; Chiral pool
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