10048-32-5Relevant articles and documents
Asymmetric synthesis of goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid via sequential allylboration-esterification ring-closing metathesis reactions
Ramachandran, P. Veeraraghavan,Reddy, M. Venkat Ram,Brown, Herbert C.
, p. 583 - 586 (2000)
Acrylic esters of homoallylic alcohols prepared in 92-97% ee via the asymmetric allylboration of appropriate aldehydes with B- allyldiisopinocampheylborane, when refluxed in dichloromethane in the presence of 10 mol% of Grubbs' catalyst provided the natural enantiomers of (S)-(+)-parasorbic acid, (R)-(-)-massoia lactone, and (R)-(+)goniothalamin. (S)-(-)-Hexadecanolide was prepared by hydrogenating the corresponding lactenone synthesized using the above sequence. (C) 2000 Elsevier Science Ltd.
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)
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.
Baker's Yeast Mediated Bioreduction of Prochiral Ketones Having 6-(4-Oxo-1,3-dioxinyl) Group
Sakaki, Jun-ichi,Suzuki, Miwako,Kobayashi, Satoshi,Sato, Masayuki,Kaneko, Chikara
, p. 901 - 904 (1990)
Prochiral ketones having 6-(4-oxo-1,3-dioxinyl) group as one terminal unit by fermenting baker's yeast gave chiral alcohols, which could be convertible to optically active hydroxyesters, β-ketoesters, and lactones.
Synthetic studies on marineosins based on a direct coupling reaction of pyrrole and δ-lactone
Fukuda, Hayato,Hatakeyama, Susumi,Ishihara, Jun,Komine, Keita,Morii, Yuki,Suga, Akihisa,Yamamoto, Kohei
, p. 46 - 59 (2020/01/28)
A promising precursor of marineosins A and B, unusual macrocyclic pyrrole and spiroiminal alkaloids isolated from marine microorganism has been synthesized employing a direct coupling of pyrrole and δ-lactone.
Enantiomerically pure allylboronic esters as versatile reagents in the enantioselective synthesis of dihydro-α-pyrone-containing natural products
Bartlett, Sean,Boese, Dietrich,Ghori, Daniel,Mechsner, Bastian,Pietruszka, Joerg
, p. 1106 - 1114 (2013/05/21)
A short and efficient enantio- and diastereoselective synthesis of different representatives from the class of dihydro-α-pyrone natural products, including both enantiomers of goniothalamin, massoia lactone, parasorbic acid, and some derivatives is presented. It is based on the application of enantiopure α-chiral allylboronic esters in allyl additions. Georg Thieme Verlag Stuttgart New York.