587-63-3Relevant articles and documents
Asymmetric synthesis of (S)-dihydrokavain from l-malic acid
Eskici, Mustafa,Karanfil, Abdullah,?zer, M. Sabih,Kabak, Yal??n,Durucasu, ?nci
, p. 2382 - 2390 (2018/10/20)
A practical and efficient asymmetric synthesis of (S)-dihydrokavain from known ethyl (S)-2-hydroxy-4-phenylbutanoate which is, in turn, readily available from l-malic acid as a cheap chiral pool material is described using regioselective ring-opening of the 1,2-cyclic sulfate with lithium-3,3,3-triethoxypropiolate and subsequent HgO/H2SO4-mediated lactonization as the key steps. Its opposite enantiomer (R)-dihydrokavain was also synthesized from d-malic acid using the same sequences of reactions for the purpose of optical purity determination.
Efficient enantioselective hetero-diels-alder reaction of brassard's diene with aliphatic aldehydes: A one-step synthesis of (R)-(+)-kavain and (S)-(+)-dihydrokavain
Lin, Lili,Chen, Zhenling,Yang, Xu,Liu, Xiaohua,Feng, Xiaoming
supporting information; scheme or table, p. 1311 - 1314 (2009/04/06)
An efficient catalytic asymmetric hetero-Diels-Alder reaction of Brassard's diene with aliphatic aldehydes was reported The catalyst which was generated from (R)-BINOL, Ti(i-PrO)4, and 4-picolyl chloride hydrochloride, promoted the reaction smoothly to afford the corresponding α, β-unsaturated λ-lactone derivatives in moderate-to-good yields (46-79%) with high enantioselectivities (up to 88% ee) Natural products (R)-(+)-kavain (70% ee, > 99% ee after single re crystallization) and (S)-(+)-dihydrokavain (84% ee) were also prepared in one step by using this methodology.
Chemoenzymatic synthesis of enantiomerically enriched kavalactones
Kamal, Ahmed,Krishnaji, Tadiparthi,Khanna, G.B. Ramesh
, p. 8657 - 8660 (2007/10/03)
Lipase-mediated kinetic resolution of methyl-3-hydroxy-5-phenylpentanoate and (6E)-ethyl 5-hydroxy-3-oxo-7-phenylhept-6-enoate is described in high enantiomeric excess and good yields. The effect of different lipases in different solvents has been screened using different acylating agents. This protocol has been extended for the preparation of enantiomerically pure biologically important kavalactones.