71582-80-4Relevant academic research and scientific papers
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
Stereoselective synthesis of marine antibiotic (-)-malyngolide and its stereoisomers.
Ichimoto,Machiya,Kirihata,Ueda
, p. 657 - 662 (1990)
A convenient synthetic method for the marine antibiotic (-)-malyngolide and its stereoisomers was accomplished from a chiral alpha-alkoxyketone (4), which was readily available as a chiron. Chiral quaternary carbon synthons (5a) and (5b) as the key intermediates were constructed by the chelation controlled addition of Grignard reagent to 4. The diastereomeric mixture of 5a and 5b was readily transformed into a separable mixture of lactones (7a) and (7b), each of which could be easily separated by silica-gel column chromatography. (-)-Malyngolide and its three stereoisomers were obtained in optically pure form without the need for optical resolution.
Novel Synthesis of (-)-Malyngolide using Reactions of Alkylidene Carbenes
Ohira, Susumu,Moritani, Masanori,Ida, Takahiro,Yamato, Masatoshi
, p. 1299 - 1300 (1993)
(-)-Malyngolide has been synthesized using three different reactions of alkylidene carbenes, generated by alkenation of carbonyl compounds with dimethyl diazomethylphosphonate.
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.
Asymmetric hydrogen transfer protocol for a synthesis of (+)-frontalin and (-)-malyngolide
Mikie Kanada, Regina,Taniguchi, Takahiko,Ogasawara, Kunio
, p. 3631 - 3635 (2000)
An insect aggregate pheromone (+)-frontalin and a marine antibiotic (-)- malyngolide, both bearing a quaternary stereogenic center in their molecules, have been synthesized in diastereocontrolled manner by employing a catalytic asymmetric hydrogen transfer reaction as the key step. An inversion protocol allowing enantioconvergent use of the other enantiomeric resolved product has also been devised. (C) 2000 Elsevier Science Ltd.
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].
Biocatalytic Approach for the Total Synthesis of (-)-Malyngolide and Its C(5)-Epimer
Srivastava, Nikhil,Subba Reddy, Basi V.
, p. 267 - 272 (2016/05/02)
An enzymatic approach has been successfully utilized in the total synthesis of (-)-malyngolide and its C(5)-epimer. The required configuration was established by an enzymatic kinetic resolution and Sharpless asymmetric dihydroxylation.
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
D- and L-erythrose as sources of chiral quaternary carbon centers. Total synthesis of (-)-malyngolide and (+)-tanikolide
Koumbis, Alexandros E.,Dieti, Kyriaki M.,Vikentiou, Myrofora G.,Gallos, John K.
, p. 2513 - 2516 (2007/10/03)
A highly efficient and versatile approach was applied for the total synthesis of the marine natural products (-)-malyngolide and (+)-tanikolide from isopropylidene L- and D-erythrose, using a common strategy.
