308358-04-5Relevant articles and documents
Total Synthesis of (-)-Carinatine A and (+)-Lycopladine A
Meng, Lingxing
, p. 7784 - 7789 (2016)
An efficient synthesis of two Lycopodium alkaloids, (-)-carinatine A and (+)-lycopladine A, is achieved in eight steps. The synthesis features an intramolecular aldol reaction for assembling the 6,5-fused ring system, a subsequent Tsuji-Trost allylation for generating a quarternary carbon center, and a 6π-electrocyclization to form the pyridine ring.
Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids
Haley, Hannah M. S.,Payer, Stefan E.,Papidocha, Sven M.,Clemens, Simon,Nyenhuis, Jonathan,Sarpong, Richmond
supporting information, p. 4732 - 4740 (2021/04/07)
Nitrogen heterocycles (azacycles) are common structural motifs in numerous pharmaceuticals, agrochemicals, and natural products. Many powerful methods have been developed and continue to be advanced for the selective installation and modification of nitrogen heterocycles through C-H functionalization and C-C cleavage approaches, revealing new strategies for the synthesis of targets containing these structural entities. Here, we report the first total syntheses of the lycodine-type Lycopodium alkaloids casuarinine H, lycoplatyrine B, lycoplatyrine A, and lycopladine F as well as the total synthesis of 8,15-dihydrohuperzine A through bioinspired late-stage diversification of a readily accessible common precursor, N-desmethyl-β-obscurine. Key steps in the syntheses include oxidative C-C bond cleavage of a piperidine ring in the core structure of the obscurine intermediate and site-selective C-H borylation of a pyridine nucleus to enable cross-coupling reactions.
Efforts toward the synthesis of (+)-Lyconadin A
Karella, Satish,Raghavan, Sadagopan
, (2020/08/10)
Abstract: Synthetic efforts toward the synthesis of (+)-lyconadin A are described. B-Alkyl Suzuki coupling is utilized for combining 2-iodo cyclohexenone with the piperidine subunit. The piperidine subunit is derived from 5-bromo-3-nicotinic acid, and iod
A concise asymmetric total synthesis of (+)-fawcettimine
Zeng, Xin,Jia, Zhuqing,Qiu, Fayang G.
supporting information, (2020/09/16)
A straightforward and stereocontrolled total synthesis of (+)-fawcettimine was accomplished from the known (R)-5-methyl-2-cyclohexen-one in 11 steps. The synthesis features a palladium mediated cycloalkenylation of a silyl enol ether for assembling the 6/
The first asymmetric total synthesis of lycoposerramine-R
Ishida, Hiroaki,Kimura, Shinya,Kogure, Noriyuki,Kitajima, Mariko,Takayama, Hiromitsu
, p. 7762 - 7771 (2015/07/15)
The first asymmetric total synthesis of lycoposerramine-R, a Lycopodium alkaloid possessing a novel skeleton, was accomplished by a strategy featuring the stereoselective intramolecular aldol cyclization giving a cis-fused 5/6 bicyclic skeleton and a new method for the construction of the pyridone ring via the aza-Wittig reaction.
Syntheses of (+)-complanadine A and lycodine derivatives by regioselective [2 + 2 + 2] cycloadditions
Yuan, Changxia,Chang, Chih-Tsung,Siegel, Dionicio
supporting information, p. 5647 - 5668 (2013/07/26)
The dimeric alkaloid complanadine A has shown promise in regenerative science, promoting neuronal growth by inducing the secretion of growth factors from glial cells. Through the use of tandem, cobalt-mediated [2 + 2 + 2] cycloaddition reactions, two synthetic routes have been developed with different sequences for the formation of the unsymmetric bipyridyl core. The regioselective formation of each of the pyridines was achieved based on the inherent selectivity of the molecules or by reversing the regioselectivity through the addition of Lewis bases. This strategy has been successfully employed to provide laboratory access to complanadine A as well as structurally related compounds possessing the lycodine core.
A new approach to the bicyclo[3.3.1]nonane framework of huperzine A-like molecules via palladium-catalyzed intramolecular γ-arylation
Ding, Rui,Lu, Yunyu,Yao, Hequan,Sun, Bingfeng,Lin, Guoqiang
scheme or table, p. 1097 - 1100 (2012/08/28)
In our synthetic studies toward huperzine A, a diastereoselective α′-alkylation of the α-amido-γ-methyl hexenone 4 was realized through a dianion intermediate which significantly enhanced the reactivity. Under the attempted Heck reaction conditions, an unexpected and unprecedented palladium-catalyzed intramolecular γ-arylation of 3 was observed, which generated 18 with bicyclo[3.3.1]nonane framework in satisfactory yield.
Total synthesis of (+)-fawcettidine
Kozak, Jennifer A.,Dake, Gregory R.
scheme or table, p. 4221 - 4223 (2009/03/11)
(Chemical Equation Presented) Alkaloids alchemy: A synthesis of the Lycopodium alkaloid (+)-fawcettidine (see structure) has been developed which requires 16 steps from (R)-(+)-pulegone as the chiral starting material. Key steps include a platinum(II)-cat
Synthesis of termini-differentiated 6-carbon stereotetrads: An alkylative oxidation strategy for preparation of the C21-C26 segment of apoptolidin
Chen, Yuzhong,Evarts Jr., Jerry B.,Torres, Eduardo,Fuchs, Philip L.
, p. 3571 - 3574 (2007/10/03)
(graph presented) Two methods have been developed for the synthesis of epoxide 36. The first uses (+)-pulegone 25 as an enantiopure starting material and introduces the requisite intricacy of target 22 in 12 operations. The second method employs an enanti
Epoxidation of α,β-Unsaturated Ketones Using Hydrogen Peroxide in the Presence of Basic Hydrotalcite Catalysts
Yamaguchi, Kazuya,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
, p. 6897 - 6903 (2007/10/03)
The basic layered hydrotalcites have been used as catalysts for the epoxidation of α,β-unsaturated ketones in heterogeneous reaction media using hydrogen peroxide as an oxidant. A wide variety of α,β-unsaturated ketones were oxidized to the corresponding epoxyketones in excellent yields under mild reaction conditions. For example, 2-cyclohexen-1-one gave 2,3-epoxycyclohexanone in 91% yield at 40°C for 5 h with high efficiency in hydrogen peroxide. The catalytic activity of the hydrotalcites increased as the basicity of their surfaces increased. In the case of the epoxidation of less reactive substrates, adding a cationic surfactant such as n-dodecyltrimethylammonium bromide (DTMAB) to the above oxidation system accelerated the epoxidation reaction. These hydrotalcite catalysts were easily separated from the reaction mixture and were reusable.