18409-17-1Relevant articles and documents
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Kow,R.,Rathke,M.W.
, p. 2715 - 2716 (1973)
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Asymmetric Total Syntheses of Two Possible Diastereomers of Gliomasolide e and Its Structural Elucidation
Reddy, Ramidi Gopal,Venkateshwarlu, Ravula,Ramakrishna, Kallaganti V. S.,Yadav, Jhillu S.,Mohapatra, Debendra K.
, p. 1053 - 1063 (2017)
The first total syntheses of two possible diastereomers of gliomasolide E, a 14-membered macrolides isolated from the marine sponge Phakellia fusca Thiele, which was collected from the South China Sea, is reported. Highlights of the synthesis include macrolactonization through intramolecular Horner-Wadsworth-Emmons olefination, Yamaguchi-Hirao alkynylation, and base-induced elimination reactions for propargyl alcohol synthesis as the key reactions. Detailed comparison of their 1H and 13C NMR (1D and 2D NMR data) and specific rotation with those of the natural product revealed that the absolute stereochemistry of gliomasolide E should be (2E,5R,7R,9R,13R).
Production of 2-Octenyl Radicals from the Fe(III)*Bleomycin-Mediated Fragmentation of 10-Hydroperoxy-8,12-octadecadienoic Acid
Natrajan, Anand,Hecht, Sidney M.
, p. 5239 - 5241 (1991)
The Fe(III)*BLM-mediated fragmentation of 10-hydroperoxy-8,12-octadecadienoic acid was demonstrated unambiguously to occur via homolytic O-O bond scission.
CuBr2-catalyzed diastereoselective allylation: Total synthesis of decytospolides A and B and their C6-epimers
Choudhury, Utkal Mani,Mallampudi, N. Arjunreddy,Mohapatra, Debendra K.,Padhi, Birakishore,Reddy, G. Sudhakar
, p. 2685 - 2695 (2020/04/17)
An efficient CuBr2-catalyzed diastereoselective allylation of a cyclic hemiacetal with allyltrimethylsilane as a nucleophile has been developed. The protocol offers a cost effective, protecting group tolerant, and operationally simple approach to 2,6-trans-disubstituted tetrahydropyran with excellent diastereoselectivity. Furthermore, the application of this methodology has been demonstrated in the total synthesis of decytospolides A and B and their C6-epimers.
Total Synthesis of Prostaglandin 15d-PGJ2 and Investigation of its Effect on the Secretion of IL-6 and IL-12
Egger, Julian,Fischer, Stefan,Bretscher, Peter,Freigang, Stefan,Kopf, Manfred,Carreira, Erick M.
supporting information, p. 4340 - 4343 (2015/09/15)
An efficient synthesis of 15-deoxy-Δ12,14-prostaglandin J2 (15d-PGJ2, 1) is reported. The route described allows for diversification of the parent structure to prepare seven analogues of 1 in which the positioning of electrophilic sites is varied. These analogues were tested in SAR studies for their ability to reduce the secretion of proinflammatory cytokines. It was shown that the endocyclic enone is crucial for the bioactivity investigated and that the conjugated ω-side chain serves in a reinforcing manner.
