Highly enantioselective hydrogenation of exocyclic double bond of N-tosyloxazolidinones catalyzed by a neutral rhodium complex and its synthetic applications

Tetrahedron ◽  
2006 ◽  
Vol 62 (39) ◽  
pp. 9237-9246 ◽  
Author(s):  
Zengming Shen ◽  
Xiyan Lu ◽  
Aiwen Lei
Keyword(s):  
Double Bond ◽  
Enantioselective Hydrogenation ◽  
Rhodium Complex ◽  
Exocyclic Double Bond

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.

Formation of Dihydroaza-azulanones Possessing Spirocyclic Moieties: [8+2] Type Cycloaddition Reactions of Iminotropones to an Exocyclic Double Bond of 8-Oxoheptafulvene

Heterocycles ◽  
1995 ◽  
Vol 41 (10) ◽  
pp. 2181 ◽  
Author(s):  
Katsuhiro Saito ◽  
Yuka Saito ◽  
Masayuki Tomita ◽  
Hiroshi Taniguchi ◽  
Hirofumi Okabayashi
Keyword(s):  
Double Bond ◽  
Exocyclic Double Bond ◽  
Cycloaddition Reactions

Structurally original oxathioethers macrocycles containing an exocyclic double-bond: synthesis, characterization, reactivity, and coordination

Tetrahedron ◽  
2014 ◽  
Vol 70 (35) ◽  
pp. 5650-5658 ◽  
Author(s):  
Guillaume Carel ◽  
Alina Saponar ◽  
Nathalie Saffon ◽  
Marc Vedrenne ◽  
Stéphane Massou ◽  
...  
Keyword(s):  
Double Bond ◽  
Exocyclic Double Bond
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