71582-80-4Relevant articles and documents
Stereoselective synthesis of a chiral synthon, 2,2,5-trisubstituted tetrahydropyran, based on simultaneous 1,3- and 1,6-asymmetric induction via nucleophilic acetal cleavage reaction of the bicyclic acetal: A total synthesis of (-)-malyngolide
Maezaki, Naoyoshi,Matsumori, Yuki,Shogaki, Takeshi,Soejima, Motohiro,Tanaka, Tetsuaki,Ohishi, Hirofumi,Iwata, Chuzo
, p. 1755 - 1756 (1997)
A chiral 2,2,5-trisubstituted tetrahydropyran is synthesised efficiently via facial and group selective nucleophilic acetal cleavage reaction of a bicyclic acetal, wherein simultaneous 1,3- and 1,6-asymmetric induction from a sulfinyl chirality is accompl
Synthesis of (-)-malyngolide from D-lactose
Matsuo,Hasuike,Kado
, p. 2847 - 2849 (1990)
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An Enantiocontrolled Synthesis of (-)-Malyngolide
Honda, Toshio,Imai, Minako,Keino, Katsuyuki,Tsubuki, Masayoshi
, p. 2677 - 2680 (1990)
Enantioselective synthesis of (-)-malyngolide (1) was accomplished by employing diastereoselective addition of nonylmagnesium bromide to the 2-acylfuran derivative (4), followed by a ring transformation of the resulting optically active 2-furylalcohol (5) to give the pyranone derivative (7) as key step.
Novel asymmetric syntheses of (-)-malyngolide and (+)-epi-malyngolide
Enders, Dieter,Knopp, Monika
, p. 5805 - 5818 (1996)
The diastereo- and enantioselective synthesis of (-)-malyngolide [(S,R)-1], an antibiotic against Mycobacterium smegmatis and Streptococcus pyogenes, using the asymmetric Carroll rearrangement as key step is described. Furthermore, the diastereo- and enantioselective synthesis by double α,α'-alkylation using SAMP/RAMP hydrazone methodology affords the diastereomer (+)-epi-malyngolide [(S,S)-1].
A new asymmetric total synthesis of enantiopure (-)-malyngolide
Miyamoto, Hidetoshi,Iwamoto, Mitsuhiro,Nakada, Masahisa
, p. 61 - 68 (2007/10/03)
A new asymmetric total synthesis of (-)-malyngolide is described. This synthesis is based on the originally developed catalytic asymmetric IMCP reaction; that is, α-diazo-β-keto sulfone (13) was successfully converted to cyclopropane (12) in 92% yield wit
Stereoselective synthesis of (-)-malyngolide, (+)-malyngolide and (+)-tanikolide using ring-closing metathesis
Carda, Miguel,Rodríguez, Santiago,Castillo, Encarnación,Bellido, Alejandro,Díaz-Oltra, Santiago,Marco, J. Alberto
, p. 857 - 864 (2007/10/03)
The stereoselective syntheses of the naturally occurring δ-lactones (+)-tanikolide and (-)-malyngolide as well as of the unnatural (+)-enantiomer of the latter are described. Key steps in each of these syntheses were stereoselective additions of organomet