Studies on the Total Synthesis of Antibiotic Macrolactin S: A Conventional Approach for the Synthesis of the C1–C9 and C10–C24 Fragments

Synthesis ◽  
2017 ◽  
Vol 50 (03) ◽  
pp. 663-675
Author(s):  
Pabbaraja Srihari ◽  
Ramakrishna Sayini
Keyword(s):  
Total Synthesis ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Addition Reaction ◽  
Epoxide Ring ◽  
Epoxide Ring Opening ◽  
Ring Opening Reaction ◽  
Nucleophilic Addition Reaction ◽  
Convergent Approach ◽  
Key Steps

The C1–C9 and C10–C24 segments of the 24-membered polyene macrolide macrolactin S were synthesized by routes involving an epoxide-ring-opening reaction, an Ohira–Bestmann alkyne formation, a chelation-controlled nucleophilic addition reaction, and a Still–Gennari olefination as key steps. A chiron approach , starting from readily available glucose diacetonide, was used to synthesize a key intermediate, and a convergent approach was adopted for the synthesis of the key C10–C24 fragment.

A protecting group free and scalable approach towards total synthesis of (−)-venlafaxine

RSC Advances ◽  
2014 ◽  
Vol 4 (28) ◽  
pp. 14468-14470 ◽  
Author(s):  
Subhash P. Chavan ◽  
Kailash P. Pawar ◽  
Sumanta Garai
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Epoxide Ring ◽  
Protecting Group ◽  
Asymmetric Total Synthesis ◽  
Epoxide Ring Opening ◽  
Key Steps

A protecting group free asymmetric total synthesis of (−)-venlafaxine is reported. The strategy employs Sharpless epoxidation and regio-selective epoxide ring opening by an in situ generated Gilman reagent as key steps. This paper reports a 53% overall yield in 6 steps for total synthesis of (−)-venlafaxine.

First Total Synthesis of a Fluorinated Calystegin

2010 ◽  
Vol 65 (4) ◽  
pp. 445-451 ◽  
Author(s):  
René Csuk ◽  
Erik Prell ◽  
Stefan Reißmann ◽  
Claudia Korb
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Competitive Inhibitor ◽  
Ring Closure ◽  
Target Compound ◽  
Metathesis Reaction ◽  
Grubbs Catalyst ◽  
Ring Opening Reaction ◽  
Ultrasound Assisted ◽  
Key Steps

A straightforward chiral pool synthesis for the first fluorinated calystegin is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs’ catalyst-mediated ring closure metathesis reaction. The target compound is a selective and competitive inhibitor for a β -glycosidase.

scholarly journals Synthesis and catalytic testing of Lewis acidic nano-MFI zeolites for the epoxide ring opening reaction with alcohol

2018 ◽  
Vol 566 ◽  
pp. 25-32 ◽  
Author(s):  
Aamena Parulkar ◽  
Rutuja Joshi ◽  
Nitish Deshpande ◽  
Nicholas A. Brunelli
Keyword(s):  
Ring Opening ◽  
Epoxide Ring ◽  
Epoxide Ring Opening ◽  
Ring Opening Reaction ◽  
Mfi Zeolites

scholarly journals Correction: Epoxide ring-opening reaction promoted by ionic liquid reactivity: interplay of experimental and theoretical studies

2019 ◽  
Vol 9 (22) ◽  
pp. 6532-6532
Author(s):  
Shengxin Chen ◽  
Guixiang Zeng ◽  
Yingwei Li ◽  
Bin He ◽  
Ruixia Liu ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Ring Opening ◽  
Epoxide Ring ◽  
Theoretical Studies ◽  
Epoxide Ring Opening ◽  
Ring Opening Reaction ◽  
Experimental And Theoretical Studies

Correction for ‘Epoxide ring-opening reaction promoted by ionic liquid reactivity: interplay of experimental and theoretical studies’ by Shengxin Chen et al., Catal. Sci. Technol., 2019, DOI: 10.1039/c9cy00953a.

Total Synthesis of (–)-Alstofolinine A: Selected Furan Oxidation/ Cyclization Cascade

Synlett ◽  
2019 ◽  
Vol 31 (01) ◽  
pp. 7-12 ◽  
Author(s):  
Ye Zhang ◽  
Lei Zhang ◽  
Xiangbing Qi
Keyword(s):  
Total Synthesis ◽  
Common Core ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Asymmetric Total Synthesis ◽  
Ring Systems ◽  
Synthetic Strategy ◽  
Nucleophilic Addition Reaction

Indole-fused tetracyclic ring systems containing nitrogen atoms are common core skeletons of many indole alkaloids such as sarpagine, macroline, and ajmaline. Efficient and stereoselective construction of these ring systems can promote the development of the corresponding alkaloid syntheses. In this article, we briefly summarize our current progress toward the application of the aza-Achmatowicz reaction and indole nucleophilic addition reaction cascade for the first asymmetric total synthesis of the macroline-type indole alkaloid (–)-Alstofolinine A. Our synthetic strategy is based on furan oxidation/rearrangement and proceeds from easily accessible materials such as indole and furan derivatives.

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.

First total synthesis of the highly potent antitumor lactones 8-chlorogoniodiol and parvistone A: Exploiting a bioinspired late-stage epoxide ring-opening

2017 ◽  
Vol 28 (2) ◽  
pp. 246-249 ◽  
Author(s):  
Perla Ramesh ◽  
Yarram Narasimha Reddy ◽  
Thatikonda Narendar Reddy ◽  
Navuluri Srinivasu
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Ring Opening ◽  
Epoxide Ring ◽  
Epoxide Ring Opening

ChemInform Abstract: In vivo Antimalarial Activity of Novel 2-Hydroxy-3-anilino-1,4-naphthoquinones Obtained by Epoxide Ring-Opening Reaction.

ChemInform ◽  
2013 ◽  
Vol 44 (49) ◽  
pp. no-no
Author(s):  
Lucas Cunha Dias de Rezende ◽  
Fernando Fumagalli ◽  
Marraiana Schiavon Bortolin ◽  
Marianne Garcia de Oliveira ◽  
Murilo Helder de Paula ◽  
...  
Keyword(s):  
Ring Opening ◽  
Antimalarial Activity ◽  
Epoxide Ring ◽  
Epoxide Ring Opening ◽  
Ring Opening Reaction
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