203131-19-5Relevant articles and documents
Biomimetic total synthesis of litseaverticillols B, E, I, and J and structural reassignment of litseaverticillol E
Vassilikogiannakis, Georgios,Margaros, Ioannis,Montagnon, Tamsyn
, p. 2039 - 2042 (2004)
Equation presented. The first total synthesis of litseaverticillols B (1), E (2), I (4), and J (5) as well as the structural reassignment of litseaverticillol E (2) have been achieved by means of a biomimetic sequence of transformations during which a [4 + 2]-initiated reaction cascade and an ene reaction, both involving singlet oxygen (1O2), formed key steps. The reassignment of the structure of litseaverticillol E (3) to include an allylic hydroperoxide provides strong support for our biogenetic hypothesis.
Illustrating the power of singlet oxygen chemistry in a synthetic context: Biomimetic syntheses of litseaverticillols A-G, I and J and the structural reassignment of litseaverticillol E
Vassilikogiannakis, Georgios,Margaros, Ioannis,Montagnon, Tamsyn,Stratakis, Manolis
, p. 5899 - 5907 (2005)
Biomimetic syntheses of the litseaverticillols A-G, I and J are reported herein. The syntheses rely heavily on the application of two different modes of reaction for photochemically generated singlet oxygen, namely, the [4+2] cycloaddition of singlet oxygen (1O2) with furans and the ene reaction of 1O2 with double bonds. The highlight of these syntheses is a one-pot cascade sequence, involving five synthetic operations initiated by a [4+2] reaction, to form the fully functionalised litseaverticillol core. A series of regioselective ene reactions are then used to appositely functionalise the side chains. The synthesis of litseaverticillol E (both its originally proposed and its actual structures) allows a structural reassignment of this natural product.
Synthesis of Penta-2,4-dien-1-imines and 1,2-Dihydropyridines by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-(Siloxy)furans
Funakoshi, Yuuta,Miura, Tomoya,Murakami, Masahiro
supporting information, p. 6284 - 6287 (2016/12/23)
A rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with 2-(siloxy)furans is reported. Either open-chain penta-2,4-dien-1-imines or cyclic 1,2-dihydropyridines are selectively obtained depending on the ligand on rhodium(II).