scholarly journals Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family

2015 ◽  
Vol 51 (14) ◽  
pp. 2871-2873 ◽  
Author(s):  
Dattatraya H. Dethe ◽  
Rohan D. Erande ◽  
Samarpita Mahapatra ◽  
Saikat Das ◽  
Vijay Kumar B.
Keyword(s):  
Natural Products ◽  
Lewis Acid ◽  
Allylic Alcohol ◽  
Protecting Group ◽  
Total Syntheses ◽  
Acid Catalyzed

A simple, highly diastereoselective, Lewis acid catalyzed Friedel–Crafts coupling of a cyclic allylic alcohol with resorcinol derivatives has been developed.

Enantiospecific total syntheses of meroterpenoids (−)-F1839-I and (−)-corallidictyals B and D

2017 ◽  
Vol 15 (1) ◽  
pp. 65-68 ◽  
Author(s):  
Dattatraya H. Dethe ◽  
Balu D. Dherange ◽  
Saghir Ali ◽  
Mahesh M. Parsutkar
Keyword(s):  
Natural Products ◽  
Lewis Acid ◽  
Bond Formation ◽  
Environmentally Benign ◽  
Formation Reaction ◽  
Total Syntheses

Enantiospecific total syntheses of spiromeroterpenoid natural products (−)-F1839-I and (−)-corallidictyals B and D were achieved using the environmentally benign and highly atom economical Lewis acid catalysed Friedel–Crafts reaction and a highly regio- and stereoselective spirocyclic C–O bond formation reaction.

Accessing Polycyclic Terpenoids from Zerumbone via Lewis Acid Catalyzed Synthetic Strategies

Synthesis ◽  
2020 ◽  
Vol 52 (14) ◽  
pp. 2045-2064 ◽  
Author(s):  
Puthiyaparambath Sharathna ◽  
Murugan Thulasi Meenu ◽  
Kokkuvayil Vasu Radhakrishnan ◽  
Bhandara Purayil Dhanya ◽  
Greeshma Gopalan ◽  
...  
Keyword(s):  
Natural Products ◽  
Lewis Acid ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Effective Strategy ◽  
Structural Elements ◽  
Nazarov Cyclization ◽  
Active Compounds ◽  
Acid Catalyzed

We herein disclose an effective strategy for the synthesis of [5.3.0] and [6.3.0] fused polycyclic terpenoids, which are important structural elements of natural products and biologically active compounds. The method comprises of Lewis acid catalyzed interrupted Nazarov cyclization of zerumbone derivatives such as zerumbone epoxide, triazole-appended zerumbone, zerumbal, and zerumbenone with a wide substrate scope with different indoles. Zerumbone epoxide furnished [5.3.0] and [6.3.0] fused structurally diverse sesquiterpenoids and all other zerumbone derivatives furnished the [6.3.0] fused motifs.

Tandem Lewis acid catalyzed coupling/semipinacol rearrangement of allylic alcohol

2010 ◽  
Vol 53 (1) ◽  
pp. 147-149 ◽  
Author(s):  
DaoYi Yuan ◽  
YongQiang Zhang ◽  
YongQiang Tu ◽  
ZhiHua Chen ◽  
Xiong Zhao
Keyword(s):  
Lewis Acid ◽  
Allylic Alcohol ◽  
Acid Catalyzed ◽  
Semipinacol Rearrangement

Advances in catalytic and protecting-group-free total synthesis of natural products: a recent update

2020 ◽  
Vol 56 (61) ◽  
pp. 8569-8590 ◽  
Author(s):  
Rodney A. Fernandes ◽  
Praveen Kumar ◽  
Priyanka Choudhary
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Protecting Group ◽  
Feature Article ◽  
Total Syntheses

This feature article highlights the recently achieved efficient total syntheses of many natural products based on catalytic steps and protecting-group-free strategies, leading to overall economy and efficiency in synthesis.

scholarly journals Lewis Acid Mediated Cyclizations: Diastereoselective Synthesis of Six- to Eight-Membered Substituted Cyclic Ethers

Synthesis ◽  
2017 ◽  
Vol 49 (18) ◽  
pp. 4229-4246 ◽  
Author(s):  
Arun Ghosh ◽  
Anthony Tomaine ◽  
Kelsey Cantwell
Keyword(s):  
Natural Products ◽  
Drug Design ◽  
Lewis Acid ◽  
Medicinal Chemistry ◽  
Cyclic Ether ◽  
Cyclic Ethers ◽  
Diastereoselective Synthesis ◽  
Acid Catalyzed

Cyclic ethers are widely abundant in natural products. Cyclic ether templates are also utilized in drug design and medicinal chemistry. Although the synthetic processes for this class of compounds have been studied extensively with respect to five- and six-membered rings, medium-sized cyclic ethers are synthetically more challenging due to a variety of factors. Herein, we report our results on the Lewis acid catalyzed synthesis of medium-sized cyclic ethers in a diastereoselective manner.

The total synthesis of (+)-aspicilin using 2,3-butane diacetal protected butane tetrols via a chiral memory protocol

2001 ◽  
Vol 79 (11) ◽  
pp. 1668-1680 ◽  
Author(s):  
Darren J Dixon ◽  
Alison C Foster ◽  
Steven V Ley
Keyword(s):  
Total Synthesis ◽  
Lewis Acid ◽  
Selective Hydrogenation ◽  
Protecting Group ◽  
Ring Closing Metathesis ◽  
Total Syntheses ◽  
Key Steps

The total syntheses of the polyhydroxylated macrolactone (+)-aspicilin and a diastereoisomer have been achieved via a concise route, starting from the spatially desymmetrized (R',R',R,S)-2,3-butanediacetal-protected butane tetrol 13. The key steps include a regioselective silyl protection of 13 and a stereoselective Lewis acid mediated addition of allyltributylstannane to the equatorially disposed aldehyde of 4. Macrocyclization is achieved using ring closing metathesis, after which selective hydrogenation and protecting group removal yields the natural product.Key words: aspicilin, butanediacetal, desymmetrization, macrolactone, metathesis.

Total syntheses of (±)-taiwaniaquinol D and (±)-taiwaniaquinone D via a key Lewis acid-catalyzed Nazarov type cyclization

2016 ◽  
Vol 57 (29) ◽  
pp. 3179-3184 ◽  
Author(s):  
Badrinath N. Kakde ◽  
Amarchand Parida ◽  
Pooja Kumari ◽  
Alakesh Bisai
Keyword(s):  
Lewis Acid ◽  
Total Syntheses ◽  
Acid Catalyzed
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