188924-70-1Relevant academic research and scientific papers
Synthesis of γ- and δ-lactone natural products by employing a trans-cis isomerization/lactonization strategy
Ono, Machiko,Kato, Keisuke,Akita, Hiroyuki
, p. 464 - 470 (2013/06/05)
Alkaline hydrolysis of 4-hydroxy- or/and 5-hydroxy-(2E)-alkenoate followed by acid treatment gave the corresponding (2E)-alkenoic acids which were subjected to lactone formation reaction without further purification. The crude acids were treated with 2,4,6-trichlorobenzoyl chloride in pyridine to afford ?-lactone or d-lactone, respectively, accompanied by trans-cis isomerization. By this procedure, (±)-(4,5)-trans-5-benzyloxy- 2-hexen-4-olide (90% overall yield), (S)-5-hydroxy-2-penten-4-olide (86% overall yield), (4S,5R)-5- hydroxy-2-hexen-4-olide (86% overall yield), (4R,5S)-5-hydroxy-2-hexen-4-olide (82% overall yield), (S)- parasorbic acid (58% overall yield) and natural product, (5R,7S)-7-hydroxy-2-octen-5-olide (euscapholide: 20% overall yield) were synthesized.
Strategy for Enantio- and Diastereoselective Syntheses of All Possible Stereoisomers of 1,3-Polyol Arrays Based on a Highly Catalyst-Controlled Epoxidation of α,β-Unsaturated Morpholinyl Amides: Application to Natural Product Synthesis
Tosaki, Shin-Ya,Horiuchi, Yoshihiro,Nemoto, Tetsuhiro,Ohshima, Takashi,Shibasaki, Masakatsu
, p. 1527 - 1544 (2007/10/03)
We describe a new strategy for enantio- and diastereoselective syntheses of all possible stereoisomers of 1,3-polyol arrays. This strategy relies on a highly catalyst-controlled epoxidation of α,β-unsaturated morpholinyl amides promoted by the Sm-BINOL-Ph
Enantioselective syntheses of cryptocarya triacetate, Cryptocaryolone, and cryptocaryolone diacetate
Smith, Catherine M.,O'Doherty, George A.
, p. 1959 - 1962 (2007/10/03)
(Matrix presented) The enantioselective syntheses of three natural products from Cryptocarya latifolia have been achieved in 13-15 steps from ethyl sorbate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-cat
An enantioselective synthesis of cryptocarya diacetate
Hunter, Thomas J.,O'Doherty, George A.
, p. 2777 - 2779 (2007/10/03)
(Equation presented) The enantioselective synthesis of cryptocarya diacetate has been achieved in 10 steps from ethyl sorbate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a δ-h
