First total synthesis of Lycopodium alkaloids of the magellanane group. Enantioselective total syntheses of (-)-magellanine and (+)-magellaninone

1993 ◽  
Vol 115 (7) ◽  
pp. 2992-2993 ◽  
Author(s):  
Gavin C. Hirst ◽  
Theodore O. Johnson ◽  
Larry E. Overman
Keyword(s):  
Total Synthesis ◽  
Total Syntheses ◽  
Lycopodium Alkaloids

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.

Lycopodium Alkaloids: An Intramolecular Michael Reaction Approach

Synlett ◽  
2017 ◽  
Vol 28 (17) ◽  
pp. 2212-2229 ◽  
Author(s):  
Mrinmoy Saha ◽  
Rich Carter
Keyword(s):  
Total Synthesis ◽  
Michael Reaction ◽  
Large Family ◽  
Structural Features ◽  
Total Syntheses ◽  
Michael Additions ◽  
The Core ◽  
Lycopodium Alkaloids ◽  
Rich History ◽  
Eastern Half

The Lycopodium alkaloids possess a rich history that has captured the attention of synthetic chemists across the globe. This large family consists of over 250 known natural products with diverse structural features and noteworthy biological activity. Herein, we interweave the synthetic accomplishments by others in the field with our own unified strategy to accessing multiple subfamilies of the Lycopodium alkaloids. This discussion includes lycopodine, the C10-hydroxy Lycopodium alkaloids (10-hydroxylycopodine, deacetylpaniculine and paniculine), pelletierine, cermizine D, fastigiatine, himeradine A, clavolonine and 7-hydroxylycopodine. A unifying feature of much of the work discussed within this account is the use of intramolecular Michael additions to construct key ring systems within the Lycopodium alkaloids. Examples include the use of an intramolecular keto-sulfone Michael reaction and an intramolecular heteroatom Michael reaction.1 General Background on Lycopodium Alkaloids2 Development of a Strategy for Lycopodium Alkaloids2.1 Generalized Strategy2.2 Known Syntheses of C10-Functionalized Lycopodium Alkaloids3 Quinolizidine-Type Alkaloids3.1 Background3.2 Development of the Heteroatom Michael Reaction3.3 Synthesis of the Core Lycopodine Building Block: Pelletierine3.4 Total Synthesis of Cermizine D3.5 Synthesis of the Eastern Half of Himeradine A4 Lycopodine-Type Alkaloids4.1 Total Syntheses of Lycopodine4.1.1 Earlier Racemic Syntheses4.1.2 Approach Toward the Tricyclic Skeleton of Lycopodine: Intramolecular Mannich4.1.3 Enantioselective Total Syntheses of Lycopodine4.2 Total Syntheses of Clavolonine (8-Hydroxylycopodine)4.3 Total Synthesis of 7-Hydroxylycopodine4.4 Synthetic Route for 10-Hydroxy Lycopodium Alkaloids4.4.1 Background4.4.2 Total Syntheses4.4.3 Impact of the C10-Stereochemistry5 Conclusion

scholarly journals Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3224
Author(s):  
Leander Geske ◽  
Ulrich Kauhl ◽  
Mohamed E. M. Saeed ◽  
Anja Schüffler ◽  
Eckhard Thines ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Biological Activities ◽  
Biological Evaluation ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Total Syntheses ◽  
Wittig Olefination ◽  
Starting Point ◽  
Perkin Reaction ◽  
Synthesis And Biological Evaluation

The biological activities of shancigusin C (1) and bletistrin G (2), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (1) was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G (2) was achieved by the Wittig olefination followed by several regioselective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry. The cytotoxic properties of shancigusin C (1) and bletistrin G (2) against tumor cells suggest suitability as a starting point for further structural variation.

Total syntheses and antiproliferative activities of prenostodione and its analogues

2021 ◽  
Author(s):  
Aldahir Ramos Orea ◽  
María Teresa Ramírez-Apan ◽  
Rosa M. Chávez-Santos ◽  
Rodrigo Aguayo-Ortiz ◽  
Clara I Espitia ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Indole Alkaloid ◽  
Total Syntheses ◽  
Antiproliferative Activities

A high-yielding total synthesis of the indole alkaloid prenostodione was completed in 4 steps and 44% overall yield from 1H-indole-3-carboxylic acid. The expedient syntheses of prenostodiones containing distinct substituents at...

scholarly journals Synthetic studies on the lycopodium alkaloids. IV. Total synthesis of dl-anhydrolycodoline and dl-lycopodine.

1978 ◽  
Vol 26 (10) ◽  
pp. 3150-3153 ◽  
Author(s):  
SANGWON KIM ◽  
YUKIHIDE BANDO ◽  
NOBUKO TAKAHASHI ◽  
ZENICHI HORII
Keyword(s):  
Total Synthesis ◽  
Lycopodium Alkaloids ◽  
Synthetic Studies

scholarly journals Stereoselective total syntheses of (±)-sinularene and (±)-5-epi-sinularene: a general intramolecular Diels–Alder approach to tricyclic sesquiterpenes

1985 ◽  
Vol 63 (4) ◽  
pp. 993-995 ◽  
Author(s):  
Kazimierz Antczak ◽  
John F. Kingston ◽  
Alex G. Fallis
Keyword(s):  
Double Bond ◽  
Methyl Ester ◽  
Total Synthesis ◽  
Ring System ◽  
Diels Alder ◽  
Exocyclic Double Bond ◽  
Total Syntheses ◽  
Methyl Group ◽  
Secondary Hydroxyl ◽  
Selective Hydrogenolysis

Stereoselective total synthesis of (±)-sinularene and (±)-5-epi-sinularene are described. The sequence employs a "blocked" cyclopentadiene in which the cyclopropane unit also serves as a latent methyl group. Thus intramolecular [4 + 2] cycloaddition of the substituted methyl spiro[2.4]hepta-4,6-dien-1-yl)-2-pentenoate 11 affords 5-benzyloxy-6-isopropyl-8-carbomethoxytetracyclo[5.4.01,7.02,4.02,9]undec-10-ene (12) which after selective hydrogenolysis generates the tricyclo[4.4.01,6.02,8]decane (sinularene) ring system. Removal of the secondary hydroxyl function (Ph3P/CCl4/CH3CN; H2/Pd/C), reduction of the methyl ester (LiAlH4), and introduction of the exocyclic double bond (acetate pyrolysis, 550 °C) completes the synthesis of (±)-sinularene in 14 steps from cyclopentadiene. A parallel series of reactions employing the isopropyl epimer of 12 affords (±)-5-epi-sinularene.

Recent Advances in the Total Synthesis of Clavaminols

Synthesis ◽  
2018 ◽  
Vol 50 (23) ◽  
pp. 4569-4576
Author(s):  
Tian Jin ◽  
Lu Zhao ◽  
Zhe-Bin Zheng ◽  
Xiao Liu ◽  
Liang Sun ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Research Groups ◽  
Total Syntheses ◽  
New Class ◽  
Recent Advances ◽  
Molecular Architectures ◽  
Synthetic Approaches ◽  
Long Chain

Clavaminols are a new class of long-chain 2-amino-3-­alkanols that mostly contain 2R,3S-configurations. Owing to their interesting molecular architectures and promising activities, they have ­become popular targets for synthetic organic chemists. In this review, we highlight 12 total syntheses of clavaminols from different research groups during the period 2009 to 2018.1 Introduction2 Synthetic Approaches toward Clavaminols2.1 Total Synthesis by Chemla and Colleagues (2009)2.2 Total Synthesis by Greck and Colleagues (2010)2.3 Total Synthesis by Sutherland and Zaed (2011)2.4 Total Synthesis by Huang and Colleagues (2011)2.5 Total Synthesis by Kotora and Colleagues (2012)2.6 Total Synthesis by Kumar and Colleagues (2013)2.7 Total Synthesis by Prabhavathi Devi and Colleagues (2013 and 2016)2.8 Total Synthesis by Sarabia and Colleagues (2014)2.9 Total Synthesis by Mohapatra and Colleagues (2016)2.10 Total Synthesis by Lu and Colleagues (2016)2.11 Total Synthesis by Jin and Colleagues (2017)2.12 Total Synthesis by Kumar Pandey and Colleagues (2018)3 Conclusion

scholarly journals Total syntheses of all tri-oxygenated 16-phytoprostane classes via a common precursor constructed by oxidative cyclization and alkyl–alkyl coupling reactions as the key steps

2017 ◽  
Vol 15 (44) ◽  
pp. 9408-9414 ◽  
Author(s):  
Jakub Smrček ◽  
Radek Pohl ◽  
Ullrich Jahn
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Common Precursor ◽  
Key Steps

A parallel total synthesis of 16-F1t-, 16-E1-phytoprostanes and a first synthesis of 16-D1t-phytoprostanes based on a common precursor are described.

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