De novo protecting-group-free total synthesis of (+)-muricadienin, (+)-ancepsenolide and (+)-3-hexadecyl-5-methylfuran-2(5H)-one

2016 ◽  
Vol 14 (38) ◽  
pp. 9072-9079 ◽  
Author(s):  
Rupesh A. Kunkalkar ◽  
Debasish Laha ◽  
Rodney A. Fernandes
Keyword(s):  
Total Synthesis ◽  
De Novo ◽  
Protecting Group ◽  
Ring Closing Metathesis ◽  
Type Coupling

A de novo protecting-group-free total synthesis of (+)-muricadienin, (+)-ancepsenolide and (+)-3-hexadecyl-5-methylfuran-2(5H)-one has been achieved by ring-closing-metathesis and sp–sp3 Sonogashira type coupling.

Protecting-Group-Free Total Synthesis of Anticancer (±)-Melotenine A

Synthesis ◽  
2021 ◽  
Author(s):  
Adisak Thanetchaiyakup ◽  
Hassayaporn Rattanarat ◽  
Sudaporn Aree ◽  
Tanwawan Duangthongyou ◽  
Tanin Nanok ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Human Cancer ◽  
Alder Reaction ◽  
Diels Alder ◽  
Protecting Groups ◽  
Protecting Group ◽  
Ring Closing Metathesis ◽  
Human Cancer Cell Lines ◽  
Diels Alder Reaction ◽  
Key Steps

Melotenine A, isolated from Melodinus tenuicaudatus, possesses significant anticancer activity against several human cancer cell lines. The synthesis of (±)-melotenine A was achieved without the use of any protecting groups in 11 steps with an overall yield of 7%. The key steps of our strategy were the Diels–Alder reaction to construct the tetracyclic framework and ring-closing metathesis to form the seven-membered ring of (±)-melotenine A.

scholarly journals Total Synthesis of the Antitumor Antibiotic (±)-Streptonigrin: First- and Second-Generation Routes for de Novo Pyridine Formation Using Ring-Closing Metathesis

2013 ◽  
Vol 78 (24) ◽  
pp. 12338-12350 ◽  
Author(s):  
Timothy J. Donohoe ◽  
Christopher R. Jones ◽  
Anne F. Kornahrens ◽  
Luiz C. A. Barbosa ◽  
Louise J. Walport ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Second Generation ◽  
De Novo ◽  
Antitumor Antibiotic ◽  
Ring Closing Metathesis ◽  
First And Second Generation

Total Synthesis of (±)-Streptonigrin: De Novo Construction of a Pentasubstituted Pyridine using Ring-Closing Metathesis

2011 ◽  
Vol 133 (41) ◽  
pp. 16418-16421 ◽  
Author(s):  
Timothy J. Donohoe ◽  
Christopher R. Jones ◽  
Luiz C. A. Barbosa
Keyword(s):  
Total Synthesis ◽  
De Novo ◽  
Ring Closing Metathesis

scholarly journals Rapid, two-pot procedure for the synthesis of dihydropyridinones; total synthesis of aza-goniothalamin

2020 ◽  
Vol 16 ◽  
pp. 135-139
Author(s):  
Thomas J Cogswell ◽  
Craig S Donald ◽  
Rodolfo Marquez
Keyword(s):  
Total Synthesis ◽  
Protecting Group ◽  
Ring Closing Metathesis ◽  
One Pot ◽  
High Yields

A fast, protecting-group-free synthesis of dihydropyridinones has been developed. Starting from commercially available aldehydes, a novel one-pot amidoallylation gave access to diene compounds in good yields. Ring-closing metathesis conditions were then employed to produce the target dihydropyridinones efficiently and in high yields.

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.

Protecting group directed ring-closing metathesis (RCM): the first total synthesis of an anti-malarial nonenolide

2007 ◽  
Vol 48 (14) ◽  
pp. 2621-2625 ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Dhondi K. Ramesh ◽  
Michael A. Giardello ◽  
Mukund S. Chorghade ◽  
Mukund K. Gurjar ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Protecting Group ◽  
Ring Closing Metathesis

A Total Synthesis of the Styryllactone (+)-Goniodiol from Naphthalene

2003 ◽  
Vol 56 (6) ◽  
pp. 585 ◽  
Author(s):  
Martin G. Banwell ◽  
Mark J. Coster ◽  
Alison J. Edwards ◽  
Ochitha P. Karunaratne ◽  
Jason A. Smith ◽  
...  
Keyword(s):  
Total Synthesis ◽  
First Generation ◽  
Lithium Perchlorate ◽  
Protecting Group ◽  
Microbial Oxidation ◽  
Ring Closing Metathesis ◽  
Enantiomerically Pure ◽  
Benzylic Alcohol ◽  
Acid Catalyzed ◽  
Metal Catalyzed

The cytotoxic natural product (+)-goniodiol (1) has been prepared in twelve steps from the enantiomerically pure cis-dihydrocatechol (2), which is readily obtained by microbial oxidation of naphthalene. Elaboration of compound (2) involves an initial oxidative cleavage to dialdehyde (7) followed by reduction to give diol (12). Conversion of compound (12) into acetal (17) required, inter alia, selective oxidation of the benzylic alcohol moiety followed by a metal-catalyzed decarbonylation of the resulting aldehyde. Allylation of compound (17) with allyltributylstannane in the presence of lithium perchlorate gave a ca. 2.7 : 1 mixture of alcohols (18) and (19), each of which was converted into the corresponding acrylate under standard conditions. Subjection of these ester derivatives to a ring-closing metathesis (RCM) reaction with Grubbs' first-generation catalyst gave the anticipated lactones (22) and (23). Acid-catalyzed removal of the acetonide protecting group within compound (22) then afforded (+)-goniodiol (1), while analogous deprotection of congener (23) afforded 6-epi-(+)-goniodiol (24).

ChemInform Abstract: Total Synthesis of the Antitumor Antibiotic (.+-.)-Streptonigrin: First- and Second-Generation Routes for de Novo Pyridine Formation Using Ring-Closing Metathesis.

ChemInform ◽  
2014 ◽  
Vol 45 (21) ◽  
pp. no-no
Author(s):  
Timothy J. Donohoe ◽  
Christopher R. Jones ◽  
Anne F. Kornahrens ◽  
Luiz C. A. Barbosa ◽  
Louise J. Walport ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Second Generation ◽  
De Novo ◽  
Antitumor Antibiotic ◽  
Ring Closing Metathesis ◽  
First And Second Generation

Short Protecting Group-free Syntheses of CDE Synthon of Racemic Camptothecin

2020 ◽  
Vol 17 (7) ◽  
pp. 588-591
Author(s):  
Pingxuan Shao ◽  
Wei Lu ◽  
Lei Wang
Keyword(s):  
Total Synthesis ◽  
Future Development ◽  
Protecting Group ◽  
Short Route ◽  
The Future ◽  
Tricyclic Ketone

A practical and concise total synthesis of tricyclic ketone 7 (CDE ring), a valuable intermediate for the synthesis of racemic camptothecin and analogs, was described (8 chemical steps and 29% overall yield). The synthesis starts with two inexpensive, readily available materials and is operationally simple to perform. It is worth mentioning that the reported protecting group-free synthesis, with advantages of a short route, would be helpful for the future development of industry-scale syntheses of camptothecin-family alkaloids.

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