Studies toward the Total Synthesis of Gambieric Acids, Potent Antifungal Polycyclic Ethers:  Convergent Synthesis of the CDEFG-Ring System

2005 ◽  
Vol 7 (12) ◽  
pp. 2441-2444 ◽  
Author(s):  
Kazushi Sato ◽  
Makoto Sasaki
Keyword(s):  
Total Synthesis ◽  
Ring System ◽  
Convergent Synthesis ◽  
Polycyclic Ethers

Concise Total Synthesis of Curvulone B

Synlett ◽  
2020 ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Shivalal Banoth ◽  
Utkal Mani Choudhury ◽  
Kanakaraju Marumudi ◽  
Ajit C. Kunwar
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Bond Forming ◽  
Cross Metathesis ◽  
Bond Forming Reactions ◽  
Key Steps

AbstractA concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts acylation.

ChemInform Abstract: TOTAL SYNTHESIS OF THE 6-SILASTEROID RING SYSTEM

1975 ◽  
Vol 6 (52) ◽  
pp. no-no
Author(s):  
S. BARCZA ◽  
C. W. HOFFMAN
Keyword(s):  
Total Synthesis ◽  
Ring System

scholarly journals Short, enantioselective, gram-scale synthesis of (−)-zephyranthine

2021 ◽  
Author(s):  
Yuxiang Zhao ◽  
Yanren Zhu ◽  
Guolan Ma ◽  
Qi Wei ◽  
Shaoxiong Yang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Functional Group ◽  
Ring System ◽  
System Construction ◽  
Synthesis Design

A reasonable synthesis design by strategically integrating functional group manipulation into the ring system construction resulted in a short, enantioselective, gram-scale total synthesis of (−)-zephyranthine.

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.

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