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.

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.

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.

scholarly journals Studies on asymmetric total synthesis of (−)-β-hydrastine via a chiral epoxide ring-opening cascade cyclization strategy

RSC Advances ◽  
2020 ◽  
Vol 10 (32) ◽  
pp. 18953-18958
Author(s):  
Jihui Li ◽  
Tianxiao Wu ◽  
Xinjing Song ◽  
Yang Zheng ◽  
Jiaxin Meng ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Enantioselective Synthesis ◽  
Epoxide Ring ◽  
Asymmetric Total Synthesis ◽  
Epoxide Ring Opening ◽  
Cascade Cyclization ◽  
The Core

Herein, both CF3COOH-catalyzed (86% ee) and KHMDS-catalyzed (78% ee) chiral epoxide ring-opening cascade cyclization to facile and enantioselective synthesis of the core phthalide tetrahydroisoquinoline scaffold of (−)-β-hydrastine are described.

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

Synthesis of Conjugated Trienes and Related Oxidation Products of α-Farnesene

1994 ◽  
Vol 47 (11) ◽  
pp. 1979 ◽  
Author(s):  
MA Brimble ◽  
DD Rowan ◽  
JA Spicer
Keyword(s):  
Ring Opening ◽  
Room Temperature ◽  
Oxidation Products ◽  
Epoxide Ring ◽  
Epoxide Ring Opening ◽  
Superficial Scald ◽  
Conjugated Trienes ◽  
Conjugated Triene ◽  
Cyclic Peroxide

The synthesis of conjugated trienes and related oxidation products of α- farnesene (1), principally from the epoxides of α- farnesene (1), is reported. Base-promoted ring opening of 6,7-epoxide (4) by KOBut/LiNPri2 affords the conjugated triene (2), whilst the 3,4-epoxide (5) affords trienol (7). In contrast, 10,11-epoxide (6) fails to undergo epoxide ring opening; it rearranges to the conjugated triene epoxide (8). Base-promoted ring opening of bisepoxide (9) afforded trienol epoxide (11) at -30°C, whilst cyclization to tetrahydrofurans (10a,b) occurred at room temperature. Photosensitized oxidation of 10,11-epoxide (6) followed by in situ treatment with acid gave the cyclic peroxide (3) and on reduction triol (12). Bisallylic alcohol (13) was prepared by alkylation of 3-methylsulfolene with geranial. Trienes (2) and (3) have been isolated previously as autoxidation products of α- farnesene (1) and are implicated as the causal agents of superficial scald of stored apples.

Total synthesis of the proposed structure of a polyketide from Phialomyces macrosporus

2015 ◽  
Vol 51 (17) ◽  
pp. 3586-3589 ◽  
Author(s):  
Hideki Abe ◽  
Satoko Itaya ◽  
Kei Sasaki ◽  
Toyoharu Kobayashi ◽  
Hisanaka Ito
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Furan Ring ◽  
Epoxide Ring ◽  
Epoxide Ring Opening

Total synthesis of the proposed structure of a polyketide isolated from Phialomyces macrosporus was accomplished. This synthesis features chemoselective epoxidation, regioselective epoxide ring opening, chemo- and diastereoselective dihydroxylation, and vinylation of lactone accompanied by the formation of a furan ring.

Total synthesis of (−)-depyranoversicolamide B

2015 ◽  
Vol 51 (89) ◽  
pp. 16143-16146 ◽  
Author(s):  
Wen-Fang Qin ◽  
T. Xiao ◽  
D. Zhang ◽  
Lin-Feng Deng ◽  
Y. Wang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Total Synthesis ◽  
Diels Alder Reaction ◽  
Key Steps

Asymmetric total synthesis of (−)-depyranoversicolamide B (12) is described from easily prepared chiral pyrroloindoline 21. Key steps in the synthesis are reductive ring opening of the pyrrolo ring in 21 and stereoselective intramolecular Diels–Alder reaction of 18.

scholarly journals Synthesis of Optically Active Maresin 2 and Maresin 2n-3 DPA

Synlett ◽  
2020 ◽  
Author(s):  
Narihito Ogawa ◽  
Takahito Amano ◽  
Yuichi Kobayashi
Keyword(s):  
Ring Opening ◽  
Optically Active ◽  
Epoxide Ring ◽  
Sonogashira Coupling ◽  
Epoxide Ring Opening ◽  
Lipid Metabolites ◽  
Swern Oxidation ◽  
Stereoselective Syntheses

AbstractMaresins are among the most potent antiinflammatory lipid metabolites. We report stereoselective syntheses of maresin 2 and maresin 2n-3 DPA. The anti-diol was constructed through epoxide ring opening of an optically active β,γ-epoxy aldehyde, synthesized in situ by Swern oxidation of the corresponding alcohol. Finally, the target compounds were synthesized through a Sonogashira coupling of a C9–C22 iodide and methyl (Z)-oct-4-en-7-ynoate or methyl oct-7-ynoate, respectively.

Bimetallic Radical Redox-Relay Catalysis for the Isomerization of Epoxides to Allylic Alcohols

2019 ◽  
Author(s):  
Ke-Yin Ye ◽  
Terry McCallum ◽  
Song Lin
Keyword(s):  
Ring Opening ◽  
High Reactivity ◽  
Hydrogen Atom Transfer ◽  
Organic Radicals ◽  
Epoxide Ring ◽  
Allylic Alcohols ◽  
Epoxide Ring Opening ◽  
Bond Forming ◽  
Co Catalysts ◽  
The Rich

Organic radicals are generally short-lived intermediates with exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely bimetallic radical redox-relay, in the regio- and stereoselective rearrangement of epoxides to allylic alcohols. This approach exploits the rich redox chemistry of Ti and Co complexes and merges reductive epoxide ring opening (initiation) with hydrogen atom transfer (termination). Critically, upon effecting key bond-forming and -breaking events, Ti and Co catalysts undergo proton-transfer/electron-transfer with one another to achieve turnover, thus constituting a truly synergistic dual catalytic system.<br>

Sign in / Sign up

Export Citation Format

Share Document