103957-83-1Relevant articles and documents
Unified enantioselective total syntheses of (?)-scholarisine G, (+)-melodinine E, (?)-leuconoxine and (?)-mersicarpine
Liu, Yao,Wang, Honggen
, p. 3544 - 3547 (2019)
A unified strategy enabled the enantioselective syntheses of (?)-scholarisine G, (+)-melodinine E, (?)-leuconoxine and (?)-mersicarpine from a common 2-alkylated indole intermediate bearing an all-carbon quaternary stereogenic center. The Smith-modified Madelung indole synthesis was used to couple simple o-toluidine with chiral lactone (+)-8, incorporating the key elements for further cyclizations. Lactone (+)-8 was prepared via a palladium-catalyzed intermolecular asymmetric allylic alkylation. The unified and protecting-group-free reaction sequences allowed the synthesis of these alkaloids in a maximum of 10 steps and with high efficiency.
Asymmetric Total Synthesis of Kopsiyunnanine K, a Monoterpenoid Indole Alkaloid with a Rearranged Skeleton
Tokuda, Ryoko,Okamoto, Yoshiki,Koyama, Tetsuya,Kogure, Noriyuki,Kitajima, Mariko,Takayama, Hiromitsu
, p. 3490 - 3493 (2016)
A new monoterpenoid indole alkaloid, kopsiyunnanine K, was isolated from Kopsia arborea. Its intriguing rearranged structure and absolute configuration, which were inferred from spectral data and a possible biosynthetic pathway, were determined on the bas
Synthesis of δ lactone derivatives. V. 3 Alkyl derivatives
Kurata,Tanaka,Takahashi
, p. 538 - 540 (1976)
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An intramolecular Diels-Alder approach to the synthesis of the right hand half of the ionophore antibiotic X-14547a
Edwards,Ley,Lister
, p. 361 - 364 (1981)
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Highly enantioselective iridium-catalyzed hydrogenation of α,β-unsaturated esters
Li, Jia-Qi,Quan, Xu,Andersson, Pher G.
, p. 10609 - 10616 (2012/11/07)
α,β-Unsaturated esters have been employed as substrates in iridium-catalyzed asymmetric hydrogenation. Full conversions and good to excellent enantioselectivities (up to 99 % ee) were obtained for a broad range of substrates with both aromatic- and aliphatic substituents on the prochiral carbon. The hydrogenated products are highly useful as building blocks in the synthesis of a variety of natural products and pharmaceuticals. Asymmetric hydrogenation: A variety of α,β-unsaturated esters were hydrogenated with high enantioselectivities (see scheme). The hydrogenated products have been used in synthetic transformations as well as in formal total syntheses. Copyright
