The Stereoselective Synthesis of the C6-C18 Fragment of Scytophycin C Employing a Novel Synthetic Methodology

Yadav, J. S.; Sunitha, V.; Reddy, B. V. Subba; Gyanchander, Eppa

doi:10.1055/s-2008-1067219

Synthesis

2008

DOI: 10.1055/s-2008-1067219

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The Stereoselective Synthesis of the C6-C18 Fragment of Scytophycin C Employing a Novel Synthetic Methodology

J. S. Yadav¹,

V. Sunitha²,

B. V. Subba Reddy³

et al.

Abstract: A novel synthetic approach towards the stereoselective synthesis of the C6-C18 fragment of the biologically active antitumor agent scytophycin C is described. The synthesis involves Marouka allylation, base-catalyzed intramolecular conjugate addition, Wittig olefination, and a tandem allylation.

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Cited by 5 publications

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Leptolyngbyolides, Cytotoxic Macrolides from the Marine Cyanobacterium Leptolyngbya sp.: Isolation, Biological Activity, and Catalytic Asymmetric Total Synthesis

Cui

Morita

Ohno

et al. 2017

Chemistry A European J

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Four new macrolactones, leptolyngbyolides A-D, were isolated from the cyanobacterium Leptolyngbya sp. collected in Okinawa, Japan. The planar structures of leptolyngbyolides were determined by extensive NMR studies, although complete assignment of the absolute configuration awaited the catalytic asymmetric total synthesis of leptolyngbyolide C. The synthesis took advantage of the catalytic asymmetric thioamide-aldol reaction using copper(I) complexed with a chiral bidentate phosphine ligand to regulate two key stereochemistries of the molecule at the outset. The present total synthesis demonstrates the utility of this reaction for the construction of complex chemical entities. In addition to the total synthesis, this work reports that leptolyngbyolides depolymerize filamentous actin (F-actin) both in vitro and in cells. Detailed biological studies suggest the probable order of F-actin depolymerization and apoptosis caused by leptolyngbyolides.

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Leptolyngbyolides, Cytotoxic Macrolides from the Marine Cyanobacterium Leptolyngbya sp.: Isolation, Biological Activity, and Catalytic Asymmetric Total Synthesis

Cui

Morita

Ohno

et al. 2017

Chemistry A European J

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Synthesis of tetrahydropyrans and related heterocycles via prins cyclization; extension to aza-prins cyclization

et al. 2010

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Catalytic asymmetric synthesis of key intermediate for scytophycin C

Cui

Watanabe

Shibasaki

2016

Tetrahedron Letters

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We achieved a formal total synthesis of scytophycin C. The synthesis demonstrates the utility of the catalytic asymmetric direct thioamide-aldol reaction for the preparation of polyketide structures, accomplished via diastereoselective allylation, and allylative cyclization as another key transformation. The reported process accesses Miyashita's key fragment corresponding to the C7-C18 framework in fewer steps (14 steps) than in previously reported syntheses.

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The Stereoselective Synthesis of the C6-C18 Fragment of Scytophycin C Employing a Novel Synthetic Methodology

Cited by 5 publications

References 5 publications

Leptolyngbyolides, Cytotoxic Macrolides from the Marine Cyanobacterium Leptolyngbya sp.: Isolation, Biological Activity, and Catalytic Asymmetric Total Synthesis

Leptolyngbyolides, Cytotoxic Macrolides from the Marine Cyanobacterium Leptolyngbya sp.: Isolation, Biological Activity, and Catalytic Asymmetric Total Synthesis

Synthesis of tetrahydropyrans and related heterocycles via prins cyclization; extension to aza-prins cyclization

Catalytic asymmetric synthesis of key intermediate for scytophycin C

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