Total Synthesis of the <i>Schisandraceae</i> Nortriterpenoid Rubriflordilactone A

Chaubet, Guilhem; Goh, Shermin S.; Mohammad, Mujahid; Gockel, B.; Cordonnier, Marie‐Caroline A.; Baars, Hannah; Phillips, Andrew W.; Anderson, Edward A.

doi:10.1002/chem.201703229

Cited by 23 publications

(8 citation statements)

References 100 publications

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“…Rubriflordilactones A and B from Schisandra rubriflora have attracted increasing attention because of their intriguing structures and promising anti-HIV activity. As shown in Figure 2E-II , Anderson ( Goh et al, 2015 ) ( Chaubet et al, 2017 ) completed the total synthesis of rubriflordilactone A (100) via a cobalt-catalyzed [2+2+2] cycloaddition as a pivotal step to close the key aromatic C-ring. This total synthesis takes 5-OPMB-pentanoic acid 100 as the starting material; Diyne 101 was prepared after a eleven-step sequence.…”

Section: The Total Synthesis Of Terpenoid Enabled By Cobalt-catalyzedmentioning

confidence: 99%

Total Synthesis of Natural Terpenoids Enabled by Cobalt Catalysis

Shu

Ai²,

Liu³

et al. 2022

Front. Chem.

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Transition metal catalysis plays an essential role in the total synthesis of natural products. Cobalt-mediated asymmetric catalysis has successfully been used as a primary or a secondary step in the total synthesis of natural products, especially terpenoids. Terpenoids represent one of the most prominent families among various categories of natural products, attracting immense attention due to their promising physiological activities. This review summarizes the recent advances toward the total synthesis of terpenoids by cobalt-mediated asymmetric catalysis, which may shed some light on their future synthetic efforts toward natural pesticides such as celanguline, azadirachtin, etc.

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Section: The Total Synthesis Of Terpenoid Enabled By Cobalt-catalyzedmentioning

confidence: 99%

Total Synthesis of Natural Terpenoids Enabled by Cobalt Catalysis

Shu

Ai²,

Liu³

et al. 2022

Front. Chem.

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“…Chaubet et al employed carbopalladation cascade reaction as a key step in the total synthesis of Rubriflordilactone A. [111] Here, bromoenediyne 568 underwent cascade cyclization to generate the multi-substituted tricyclic product 569 (91 % yield), taken forward to the desired natural product 570 (Scheme 86).…”

Section: Synthetic Applications Of Pd-mediated Cascade Reactionsmentioning

confidence: 99%

Exploiting the Versatility of Palladium Catalysis: A Modern Toolbox for Cascade Reactions

et al. 2021

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Dedicated to Professor S. Chandrasekaran on the occasion of his 75 th birthday.Palladium-catalyzed cascade cyclization received much attention in organic synthesis due to its efficiency and rapid transformation of simple starting materials into complex molecular skeletons. Celebrating the 10 th year of the prestigious Nobel prize for palladium chemistry, we witness it still proceeds strong over other transition metals for its versatility. Cascade reactions in contemporary organic synthesis reduced cost and time through careful design. It has emerged as the first choice, a powerful tool for multiple bond formations in one step with a wide range of functional group tolerance due to the deep understanding of various pathways. A variety of compounds with biological relevance with complex molecular scaffolds have been achieved using these cascade coupling reactions. This review outlines Pd-catalyzed cascade reactions from the post-Nobel era. Nevertheless, more discoveries and endless possibilities for new transformations are underway.

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“…Sun and co-workers made seminal contribution to the discovery of this fascinating class. , Not surprisingly, schinortriterpenoids have received considerable attention from the synthesis community. , Yang and colleagues pioneered the synthesis campaign by conquering schindilactone A, a formidable octacyclic schinortriterpenoid, in 2011 . A handful of syntheses of other congeners have been achieved since then, by the groups of Yang, Li, Anderson, Tang, and Ding, respectively. A series of synthetically useful strategies and methods have been developed in the related studies. − …”

Section: Introductionmentioning

confidence: 99%

Elucidation of the Structure of Pseudorubriflordilactone B by Chemical Synthesis

Yang

Sun

et al. 2019

J. Am. Chem. Soc.

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Rubriflordilactone B (1) is a schinortriterpenoid isolated by Sun and colleagues, which possesses a tetrasubstituted benzene moiety and eight stereocenters. The previous synthesis of 1 by Li and co-workers uncovered the existence of its naturally occurring stereoisomer “pseudorubriflordilactone B”. Here we report a collaborative study by the two groups that elucidates the structure of pseudorubriflordilactone B to be 16,17-bis-epi-rubriflordilactone B (26). Chemical synthesis served as an important tool in the structure determination. Taking advantage of a modular synthetic route, we systematically “mutated” the configurations of C-23, C-22, C-20, and C-16/C-17 located at the right-hand domain of 1, and thus prepared its 15 stereoisomers for spectrum comparison. The 1H NMR spectra of synthetic 26 in deuterated chloroform and pyridine were identical to those of authentic pseudorubriflordilactone B, respectively. This synthetic sample displayed anti-HIV activity (EC50 = 0.288 μM) in vitro.

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Total Synthesis of the Schisandraceae Nortriterpenoid Rubriflordilactone A

Cited by 23 publications

References 100 publications

Total Synthesis of Natural Terpenoids Enabled by Cobalt Catalysis

Total Synthesis of Natural Terpenoids Enabled by Cobalt Catalysis

Exploiting the Versatility of Palladium Catalysis: A Modern Toolbox for Cascade Reactions

Elucidation of the Structure of Pseudorubriflordilactone B by Chemical Synthesis

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