Cephalotaxus alkaloids from Torreya fargesii Franch and their cytotoxicities

Wang, Meng; Zhang, Xian-Dong; Peng, Yue-Ling; Li, Zhenghui; Ai, Hong‐Lian; Li, Ping; Feng, Tao; Liu, Ji‐Kai

doi:10.1016/j.phytol.2018.09.007

Cited by 11 publications

(13 citation statements)

References 18 publications

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“…[34] Unlike the case of 1, N-methylation of 25 by MeI afforded the 10-membered seco-dienone 35, in which the newly generated alkene ( ~ [5,6] ) was positioned outside the cyclopentenone ring (Scheme 2). During the synthesis of drupacine (18), Fuchs and co-workers used acidic conditions for the methylation of the C11 oxygenated enolone 36 and obtained the desired product 37 along with the ring-opened compound 38 (Scheme 3), [35] which was consistent with the results reported by Parry and Foxman (Scheme 2). [34] Because of the erosion of the enantiomeric excess (ee) as well as the formation of undesired ring-opened products, acidic reaction conditions have been carefully controlled or optimized for the synthesis of cephalotaxine-type alkaloids.…”

Section: Susceptibility Toward Ring Opening Of the Pentacyclic Systems Of Cephalotaxine-type Alkaloidssupporting

confidence: 83%

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Recent Total Syntheses of Cephalotaxine‐Type Alkaloids (2016–2021)

Jeon

2021

Asian J Org Chem

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Over the past decades, scientists have obtained a diverse range of interesting natural products, including alkaloids, terpenoids, and flavonoids from the genus Cephalotaxus. Among them, cephalotaxine-type alkaloids have attracted considerable attention from chemists because of their intriguing pentacyclic structures as well as the diversity of naturally occurring analogs. Notably, homoharringtonine (Trade name: Synribo®) is a pharmaceutical drug, which was approved by the FDA in 2012 for the treatment of chronic myeloid leukemia, implying that cephalotaxine-type alkaloids have medicinal value. Since the first total synthesis of cephalotaxine, almost 70 total syntheses of cephalotaxinetype alkaloids have been reported, involving various synthetic methodologies. Because of their potential as molecular platforms for the development of organic chemistry, the total synthesis of cephalotaxine-type alkaloids has been extensively studied. This review focuses on the recent 10 total syntheses of cephalotaxine-type alkaloids reported in the period, 2016-2021. In addition, synthetic hallmarks, such as common synthetic routes and ring-opening features of this class, were also addressed.

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Section: Susceptibility Toward Ring Opening Of the Pentacyclic Systems Of Cephalotaxine-type Alkaloidssupporting

confidence: 83%

“…Meanwhile, the majority of cephalotaxine-type alkaloids belong to the C11 oxygenated class. The representative member of this class is drupacine (18) which features an ether linkage between the B and D rings. [15] The ester forms of 18 include drupantonine (19), [16] cephalezomine A (20), and cephalezomine B (21).…”

Section: Introductionmentioning

confidence: 99%

Recent Total Syntheses of Cephalotaxine‐Type Alkaloids (2016–2021)

Jeon

2021

Asian J Org Chem

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“…Chemie Forschungsartikel 12170 www.angewandte.de fargesine A( 11)c ould also be obtained from 31 by the reduction of the hemiketal moiety using an excess amount of NaBH 4 .F rom 11,aseries of natural products were readily accessible.T he reduction of the lactam moiety of 11 afforded 11-hydroxycephalotaxine (4), which was converted to drupacine (3)u nder acidic conditions.T reatment of mCPBAt o3 provided cephalancetine B ( 8).…”

Section: Methodsmentioning

confidence: 99%

“…Recently,torreyafargesine A (11)a nd 11-hydroxycephalotaxinone hemiketal (12)w ere identified from Torreya fargesii Franch as new members of the C-11 oxygenated subset. [8] Them ajor structural differences among these alkaloids are the oxidation patterns on their backbone.T he biological activities of this subset of alkaloids have not yet been thoroughly explored presumably because of the limited supply from nature.…”

Section: Introductionmentioning

confidence: 99%

Collective Asymmetric Total Synthesis of C‐11 Oxygenated Cephalotaxus Alkaloids

et al. 2021

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While numerous studies pertaining to the total synthesis of Cephalotaxus alkaloids have been reported, only two strategies have been reported to date for the successful synthesis of the C‐11 oxygenated subset, due to the additional synthetic challenge posed by the remote C‐11 stereocenter. Herein, we report the collective asymmetric total synthesis of C‐11 oxygenated Cephalotaxus alkaloids using a chiral proline both as a starting material and as the only chirality source. A tetracyclic advanced intermediate was synthesized in a highly stereoselective manner from l‐proline in 8 steps involving sequential chirality transfer steps such as a diastereoselective N‐alkylation, stereospecific Stevens rearrangement and intramolecular Friedel–Crafts reaction via an unusual O‐acyloxocarbenium intermediate. From a common intermediate, the asymmetric total synthesis of six C‐11 oxygenated Cephalotaxus alkaloids was completed by a series of oxidation state adjustments.

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“…Research Articles fargesine A( 11)c ould also be obtained from 31 by the reduction of the hemiketal moiety using an excess amount of NaBH 4 .F rom 11,aseries of natural products were readily accessible.T he reduction of the lactam moiety of 11 afforded 11-hydroxycephalotaxine (4), which was converted to drupacine (3)u nder acidic conditions.T reatment of mCPBAt o3 provided cephalancetine B ( 8).…”

Section: Angewandte Chemiementioning

confidence: 99%

Collective Asymmetric Total Synthesis of C‐11 Oxygenated Cephalotaxus Alkaloids

et al. 2021

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While numerous studies pertaining to the total synthesis of Cephalotaxus alkaloids have been reported, only two strategies have been reported to date for the successful synthesis of the C-11 oxygenated subset, due to the additional synthetic challenge posed by the remote C-11 stereocenter. Herein, we report the collective asymmetric total synthesis of C-11 oxygenated Cephalotaxus alkaloids using achiral proline both as as tarting material and as the only chirality source.A tetracyclic advanced intermediate was synthesized in ah ighly stereoselective manner from l-proline in 8s teps involving sequential chirality transfer steps such as ad iastereoselective N-alkylation, stereospecific Stevens rearrangement and intramolecular Friedel-Crafts reaction via an unusual O-acyloxocarbenium intermediate.F rom ac ommon intermediate,t he asymmetric total synthesis of six C-11 oxygenated Cephalotaxus alkaloids was completed by as eries of oxidation state adjustments.

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Cephalotaxus alkaloids from Torreya fargesii Franch and their cytotoxicities

Cited by 11 publications

References 18 publications

Recent Total Syntheses of Cephalotaxine‐Type Alkaloids (2016–2021)

Recent Total Syntheses of Cephalotaxine‐Type Alkaloids (2016–2021)

Collective Asymmetric Total Synthesis of C‐11 Oxygenated Cephalotaxus Alkaloids

Collective Asymmetric Total Synthesis of C‐11 Oxygenated Cephalotaxus Alkaloids

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