Stereoselective Synthesis of (±)-Ireland Alcohol Using Titanium-Mediated [2,3]Wittig Rearrangement Product as a Starting Material

1992 ◽  
Vol 65 (7) ◽  
pp. 1841-1848 ◽  
Author(s):  
Satoru Ikegami ◽  
Hiroaki Okamura ◽  
Satoru Kuroda ◽  
Tsutomu Katsuki ◽  
Masaru Yamaguchi
Keyword(s):  
Stereoselective Synthesis ◽  
Starting Material ◽  
Rearrangement Product ◽  
Wittig Rearrangement

Stereoselective syntheses of isomers of 3,7-dimethylnonadecane, a sex pheromone of the alfalfa blotch leafminer (Agromyza frontella (Rondani))

1991 ◽  
Vol 69 (7) ◽  
pp. 1100-1106 ◽  
Author(s):  
David Miller ◽  
François Bilodeau ◽  
Robert H. Burnell
Keyword(s):  
Optical Properties ◽  
Sex Pheromone ◽  
Key Words ◽  
Stereoselective Synthesis ◽  
Starting Material ◽  
The Other ◽  
Stereogenic Center ◽  
Stereoselective Syntheses ◽  
Alfalfa Blotch Leafminer ◽  
Agromyza Frontella

Two related stereoselective syntheses of 3,7-dimethylnonadecane, a sex pheromone of the alfalfa leafminer, are described to show that pulegone can serve as a useful starting material for the preparation of chiral aliphatic isoprenoid compounds. The schemes are designed to place the stereogenic center of pulegone at C.3 in one synthesis and at C.7 in the other so that the optical properties of the products can be compared with one another and with the values calculated using Brewster's rules. Key words: chiral hydrocarbons, stereoselective synthesis, pheromone, Agromyza frontella.

Stereoselective Synthesis of 3-azabicyclo[3,3,1]Nonan-9α-yl α-(cyclopentyl-1-ene)-α-hydroxy-α-phenylacetate Hydrochloride

2005 ◽  
Vol 2005 (5) ◽  
pp. 322-323 ◽  
Author(s):  
He Liu ◽  
Xiang-Yu Han ◽  
Bo-Hua Zhong ◽  
Ke-Liang Liu
Keyword(s):  
Mandelic Acid ◽  
Phenylacetic Acid ◽  
Stereoselective Synthesis ◽  
Enantiomeric Excess ◽  
Starting Material ◽  
Sterically Hindered ◽  
Acid Esters

The isomers of α-(cyclopentyl-1-ene)-α-hydroxy-α-phenylacetic acid esters derived from 3-azabicyclo[3,3,1]nonan-9α-ol ((R)-1 and (S)-1) were obtained in high enantiomeric excess by effective stereoselective synthesis from the chiral starting material, (S) or (R)-mandelic acid using pivaldehyde as a sterically hindered reagent

Stereoselective synthesis of naturally occurring unsaturated amide alkaloids by a modified Ramberg–Bäcklund reaction

2004 ◽  
Vol 82 (5) ◽  
pp. 622-630 ◽  
Author(s):  
Yang Li ◽  
Yu Zhang ◽  
Zhi Huang ◽  
Xiaoping Cao ◽  
Kun Gao
Keyword(s):  
Potassium Hydroxide ◽  
Stereoselective Synthesis ◽  
Starting Material ◽  
Mitsunobu Reaction ◽  
Dichloromethane Solution ◽  
Naturally Occurring

A convenient and rapid approach for the synthesis of naturally occurring unsaturated amide alkaloids 1a–1n by the recently developed one-flask Ramberg–Bäcklund reaction is described. The starting material was alcohol 3, which was transformed into thiolacetate 4 using the Mitsunobu reaction. In situ cleavage of acetyl moiety of 4, followed by alkylation of the resulting thiol with appropriate chloroacetamide 5, provided the sulfide 6. Oxidation of sulfide 6 gave the corresponding sulfone 2. Treatment of the sulfone 2 with the dibromodifluoromethane in the presence of alumina-supported potassium hydroxide in dichloromethane solution afforded unsaturated amide alkaloids 1a–1n. To the best of our knowledge, the synthesis of 1e and 1i was reported for the first time.Key words: synthesis, unsaturated amide alkaloids, Ramberg–Bäcklund reaction.

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