206651-83-4Relevant articles and documents
An efficient synthesis of synargentolide A from D-mannitol
Kamal, Ahmed,Balakrishna, Moku,Reddy, Papagari Venkat,Faazil, Shaikh
, p. 2517 - 2523 (2010)
An efficient synthesis of synargentolide A is described by using d-mannitol and d-malic acid. The key features of the synthetic strategy include Wittig olefination, ring closing-metathesis reaction and cross-metathesis reaction for the formation of synarg
Total Synthesis of (R)-Argentilactone and (R)-Goniothalamin Using a Free-Radical Photoredox Approach to α,β-Unsaturated δ-Lactones
Fuentes-Pantoja, Francisco J.,Cordero-Vargas, Alejandro
supporting information, p. 4433 - 4439 (2021/08/20)
α,β-Unsaturated δ-lactones are structural motifs found in diverse pharmacologically active natural products. In fact, the unsaturated lactone is often responsible for the biological activity. Herein, we report a new approach for the syntheses of (R)-argentilactone and (R)- goniothalamin based on a photoredox intermolecular iodolactonization mediated by a photoredox process. This new approach, already employed in our research group, stands as a new methodology to achieve several natural products containing α,β-Unsaturated δ-lactones.
Stereoselective synthesis of the C1-C12 subunit of (-)-callystatin A
Raghavan, Sadagopan,Rajendar, Sheelamanthula
, p. 4371 - 4373 (2015/06/22)
A stereoselective synthesis of the C1-C12 fragment of callystatin A is disclosed. The two stereocenters at C5 and C10 were created by an organocatalytic reaction and a diastereoselective alkylation, respectively. The trisubstituted double bond was introdu
Coibacins a and b: Total synthesis and stereochemical revision
Carneiro, Vania M. T.,Avila, Carolina M.,Balunas, Marcy J.,Gerwick, William H.,Pilli, Ronaldo A.
, p. 630 - 642 (2014/04/03)
The interface between synthetic organic chemistry and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent antiinflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Additionally, we synthesized coibacin B on the basis of the assignment of configuration for coibacin A.
Total synthesis of (R)-(+)-goniothalamin and (R)-(+)-goniothalamin oxide: first application of the sulfoxide-modified Julia olefination in total synthesis
Pospí?il, Ji?í,Markó, István E.
, p. 5933 - 5937 (2007/10/03)
A short and efficient synthesis of (R)-(+)-goniothalamin 1 and (R)-(+)-goniothalamin oxide 2 is described. During this approach, the sulfoxide-modified Julia olefination was used as a key step to connect aldehyde 5 to sulfoxide 6. The desired styryl-containing adduct is obtained in good yield and with excellent E/Z selectivity.
Synthesis of (R)-(-)-argentilactone
Hansen, Trond Vidar
, p. 547 - 550 (2007/10/03)
A synthesis of (R)-(-)-argentilactone is reported starting from the (S)-enantiomer of glycidol. The synthesis is based on ring closing metathesis of the acrylic ester of (R)-1-O-(tert-butyldiphenylsilyl)-4-penten-1,2-diol 4.
Total synthesis of fostriecin (CI-920)
Boger,Ichikawa,Zhong
, p. 4161 - 4167 (2007/10/03)
The first total synthesis of the potent antitumor agent fostriecin (CI-920) is described, confirming the relative and absolute stereochemistry assignments. Fostriecin is a unique phosphate monoester which exhibits weak topoisomerase II inhibition (IC
Total synthesis of callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata
Murakami, Nobutoshi,Wang, Weiqi,Aoki, Masashi,Tsutsui, Yasuhiro,Sugimoto, Masanori,Kobayashi, Motomasa
, p. 2349 - 2352 (2007/10/03)
A first total synthesis of callystatin A (1), a potent cytotoxic polyketide from the marine sponge Callyspongia truncata, has been achieved by use of an E-selective Wittig olefination and asymmetric Evans aldol condensation as the key reactions. Thus, the
