320740-01-0Relevant articles and documents
Synthetic Studies on Amphirionin-5: Stereochemical Assignment/Reassignment of the C1-C9 Portion through Stereodivergent Synthesis
Kanto, Moemi,Sasaki, Makoto
, p. 112 - 115 (2016)
Synthesis of four diastereomers of the C1-C12 fragment of amphirionin-5 has been achieved in a convergent and stereodivergent manner. Detailed comparison of the 1H and 13C NMR data of each compound with those reported for the natural product led to not only the stereochemical assignment of the relative configuration of the C4/C5 stereogenic centers but also reassignment of the proposed relative configuration at C9 of amphirionin-5.
Stereodivergent Synthesis and Configurational Assignment of the C1-C15 Segment of Amphirionin-5
Kanto, Moemi,Sato, Sota,Tsuda, Masashi,Sasaki, Makoto
, p. 9105 - 9121 (2016)
The relative configuration of the C3-C12 portion of amphirionin-5, a novel marine polyketide with potent cell proliferation-promoting activity, was established by the stereodivergent synthesis of six diastereomeric model compounds and comparison of their NMR spectroscopic data with those reported for the natural product. This study led to the elucidation of the relative configuration between C4/C5 and C9/C12 and to the reassignment of the proposed configuration of the C9 position of amphirionin-5.
Diastereoselective and Branched-Aldehyde-Selective Tandem Hydroformylation-Hemiaminal Formation: Synthesis of Functionalized Piperidines and Amino Alcohols
Pittaway, Rachael,Fuentes, José A.,Clarke, Matthew L.
, p. 2845 - 2848 (2017/06/07)
Starting from readily available allylglycine, a tandem hydroformylation-hemiaminal formation reaction has been developed for the synthesis of chiral functionalized piperidines, with very good diastereoselectivity and branched regioselectivity using Rh/(S,
InCl3-mediated intramolecular Friedel-Crafts-type cyclization and its application to construct the [6-7-5-6] tetracyclic scaffold of liphagal
Jiang, Hao,Tian, Lufeng,Li, Zhentao,Liu, Qi,Li, Chuangchuang,Yao, Xinsheng,Yang, Zhen
experimental part, p. 36 - 42 (2012/03/22)
A unified strategy toward the construction of the [5.7.6]tricyclic skeleton of liphagal is reported, featuring InCl3-mediated intramolecular Friedel-Crafts-type cyclization.
Stereoselective synthesis of the hydrophobic side chain of scyphostatin
Takagi, Ryukichi,Tsuyumine, Shinjiro,Nishitani, Hiroko,Miyanaga, Wataru,Ohkata, Katsuo
, p. 439 - 447 (2007/10/03)
The hydrophobic side chain of scyphostatin was synthesized by a convergent synthetic pathway. The key reactions were the enzymatic asymmetric acetylation of a meso-diol, construction of the C12′-C13′ trisubstituted E-olefin moiety by Negishi coupling, and
Participation of the conjugated diene part for potent cytotoxicity of callystatin A, a spongean polyketide
Murakami, Nobutoshi,Sugimoto, Masanori,Nakajima, Tatsuo,Kawanishi, Motoyuki,Tsutsui, Yasuhiro,Kobayashi, Motomasa
, p. 2651 - 2661 (2007/10/03)
5-epi, 10-epi, 8-Deethyl, and 10-demethyl analogues of callystatin A, a potent cytotoxic spongean polyketide, were synthesized to elucidate structure-requirement for cytotoxic potency. Inversion of the asymmetric center at C-10 in callystatin A minimally
Construction of the C46-C55 Fragment of Ciguatoxin
Oka, Takahiro,Murai, Akio
, p. 1611 - 1614 (2007/10/02)
The compound with all the necessary functional groups of the KLM ring system in ciguatoxin, which is one of the most complicated toxic substances of marine origin, was synthesized stereoselectively.The crucial steps involve construction of the ethynyl alc