Asymmetric total synthesis of paecilomycin E, 10′-epi-paecilomycin E and 6′-epi-cochliomycin C

2014 ◽  
Vol 12 (41) ◽  
pp. 8257-8274 ◽  
Author(s):  
Pratik Pal ◽  
Nandan Jana ◽  
Samik Nanda
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses

The asymmetric total syntheses of paecilomycin E and its stereoisomers have been disclosed by employing the late stage Mitsunobu macrolactonization reaction.

scholarly journals Strategies and Efforts towards the Total Synthesis of Palhinine Alkaloids

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4211
Author(s):  
Yu-Yan Liang ◽  
Shi-Chao Lu ◽  
Ya-Ling Gong ◽  
Shu Xu
Keyword(s):  
Total Synthesis ◽  
Review Article ◽  
Research Groups ◽  
Asymmetric Total Synthesis ◽  
Carbon Cage ◽  
Total Syntheses ◽  
The Past ◽  
Lycopodium Alkaloids

The palhinine family of Lycopodium alkaloids were first reported in 2010, which feature an intriguing isotwistane carbon cage and a nine-membered azonane ring. It is noteworthy that the tetracyclic 5/6/6/9 skeleton was unprecedented in Lycopodium alkaloids before their seminal discovery. Over the past decade, extensive synthetic efforts stemming from seven research groups have resulted in two racemic total syntheses to date. This review article takes the opportunity to survey these efforts and achievements so as to promote further research towards the asymmetric total synthesis of palhinine alkaloids.

Asymmetric total synthesis of cryptoconcatone I

2019 ◽  
Vol 17 (14) ◽  
pp. 3552-3566 ◽  
Author(s):  
Ranjan Kumar Acharyya ◽  
Pratik Pal ◽  
Shrestha Chatterjee ◽  
Samik Nanda
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Ring Opening ◽  
Epoxide Ring ◽  
Asymmetric Total Synthesis ◽  
Epoxide Ring Opening ◽  
Cascade Cyclization ◽  
Naturally Occurring

An efficient asymmetric total synthesis of naturally occurring γ-Z-butenolide cryptoconcatone I was achieved by employing substrate-directed reductive epoxide ring opening and late-stage “Pd–Cu” catalyzed cascade cyclization.

Total Synthesis of Stemoamide, 9a-epi-Stemoamide, and 9a,10-epi-Stemoamide: Divergent Stereochemistry of the Final Methylation Steps

Synlett ◽  
2020 ◽  
Vol 31 (16) ◽  
pp. 1581-1586
Author(s):  
Imre Pápai ◽  
Petri M. Pihko ◽  
Juha H. Siitonen ◽  
Dániel Csókás
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Total Syntheses ◽  
Forming Strategy ◽  
Kinetic Selectivity

Total syntheses of stemoamide, 9a-epi-stemoamide, and 9a,10-epi-stemoamide by a convergent A + B ring-forming strategy is reported. The synthesis required a diastereoselective late-stage methylation of the ABC stemoamide core that successfully enabled access to three of the four possible diastereomeric structures. For the natural stemoamide series, the diastereoselectivity can be rationalized both by kinetic and thermodynamic arguments, whereas for the natural 9a-epi-stemoamide series, the kinetic selectivity is explained by the prepyramidalization of the relevant enolate.

Asymmetric total syntheses of naturally occurring α,β-enone-containing RALs, L-783290 and L-783277 through intramolecular base-mediated macrolactonization reaction

2020 ◽  
Vol 18 (12) ◽  
pp. 2331-2345
Author(s):  
Joy Chakraborty ◽  
Ankan Ghosh ◽  
Samik Nanda
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses ◽  
Naturally Occurring

Asymmetric total synthesis of two naturally occurring α,β-enone containing RALs, L-783290 and L-783277 is described in this article.

Asymmetric total synthesis of talienbisflavan A

2018 ◽  
Vol 16 (4) ◽  
pp. 585-592 ◽  
Author(s):  
Deng-Ming Huang ◽  
Hui-Jing Li ◽  
Jun-Hu Wang ◽  
Yan-Chao Wu
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis ◽  
Facile Synthesis ◽  
Total Syntheses ◽  
Key Steps

The first asymmetric total syntheses of talienbisflavan A and bis-8,8′-epicatechinylmethane as well as a facile synthesis of bis-8,8′-catechinylmethane has been accomplished from readily available starting materials by using a newly developed direct regioselective methylenation of catechin derivatives as one of the key steps.

scholarly journals Asymmetric Total Synthesis of C9’-epi-Sinefungin

2020 ◽  
Author(s):  
Ludovic Decultot ◽  
Rocco L. Policarpo ◽  
Brandon Wright ◽  
Danny Huang ◽  
Matthew Shair
Keyword(s):  
Total Synthesis ◽  
Small Molecule ◽  
Late Stage ◽  
Rational Design ◽  
Asymmetric Total Synthesis

The natural nucleoside (+)-sinefungin, structurally similar to cofactor S-adenosyl-L-methionine (SAM), inhibits various SAM-dependent methyltransferases (MTs). Access to sinefungin analogues could serve as the basis for the rational design of small-molecule methyltransferase inhibitors. We developed a route to the unnatural C9’ epimer of sinefungin that employed a diastereoselective Overman rearrangement to install the key C6’ amino stereocenter. The ability for late stage modification is highlighted, opening an avenue for the discovery of new MTs inhibitors.

scholarly journals Recent progress in organocatalytic asymmetric total syntheses of complex indole alkaloids

2017 ◽  
Vol 4 (3) ◽  
pp. 381-396 ◽  
Author(s):  
Jin Song ◽  
Dian-Feng Chen ◽  
Liu-Zhu Gong
Keyword(s):  
Total Synthesis ◽  
Multiple Bond ◽  
Indole Alkaloids ◽  
Cascade Reactions ◽  
Pharmaceutical Products ◽  
Chiral Molecules ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses ◽  
Asymmetric Organocatalysis ◽  
Optically Pure

Abstract Indole and its structural analogues have been frequently found in numerous alkaloids, pharmaceutical products and related materials. The enantioselective construction of these structures allows efficient total synthesis of optically pure indole alkaloids, and hence has received worldwide interest. In the past decade, asymmetric organocatalysis has been recognized as one of the most powerful strategies to create chiral molecules with high levels of stereoselectivity. In particular, organocatalytic asymmetric cascade reactions often occur with multiple bond-breaking and forming events simultaneously or sequentially, leading to the appearance of various straightforward approaches to access core structures for asymmetric total synthesis. This review will summarize recent applications of asymmetric organocatalysis in the enantioselective synthesis of indole alkaloids.

Asymmetric Total Synthesis of C9’-epi-Sinefungin

2020 ◽  
Author(s):  
Ludovic Decultot ◽  
Rocco L. Policarpo ◽  
Brandon Wright ◽  
Danny Huang ◽  
Matthew Shair
Keyword(s):  
Total Synthesis ◽  
Small Molecule ◽  
Late Stage ◽  
Rational Design ◽  
Asymmetric Total Synthesis

The natural nucleoside (+)-sinefungin, structurally similar to cofactor <i>S</i>-adenosyl-<i>L</i>-methionine (SAM), inhibits various SAM-dependent methyltransferases (MTs). Access to sinefungin analogues could serve as the basis for the rational design of small-molecule methyltransferase inhibitors. We developed a route to the unnatural C9’ epimer of sinefungin that employed a diastereoselective Overman rearrangement to install the key C6’ amino stereocenter. The ability for late stage modification is highlighted, opening an avenue for the discovery of new MT inhibitors.

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