Preparation of (4R,5S)-(5-methyl-2,2-dimethyl-1,3-dioxolane-4-ylmethyl)-phosphonium iodide. A synthetic approach to olguine: further model studies

1987 ◽  
Vol 65 (2) ◽  
pp. 332-338 ◽  
Author(s):  
Serafin Valverde ◽  
Bernardo Herradon ◽  
Rosa M. Rabanal ◽  
Manuel Martin-Lomas
Keyword(s):  
Tartaric Acid ◽  
Title Compound ◽  
Synthetic Approach ◽  
Enantiomerically Pure ◽  
Model Studies ◽  
Phosphonium Iodide ◽  
Key Steps

The enantiomerically pure title compound ((4R,5S)-(5-methyl-2,2-dimethyl-1,3-dioxolane-4-ylmethyl)-phosphonium iodide) has been synthesized starting from (R,R)-(+)-tartaric acid. The synthesis of an olguine analog has been carried out. Attempts have been made to improve the stereoselectivity and yield of key steps.

Preparation of (4R,5S)-5-methyl-2,2-dimethyl-1,3-dioxolane-4-ylmethyl)-phosphonium iodide. A synthetic approach to olguine: further model studies

1987 ◽  
Vol 65 (9) ◽  
pp. 2316-2316 ◽  
Author(s):  
S. Valverde ◽  
B. Herradón ◽  
R. M. Rabanal ◽  
M. Martín-Lomas
Keyword(s):  
Synthetic Approach ◽  
Model Studies ◽  
Phosphonium Iodide

not available

Enantioselective Synthesis of the Sex Pheromone of Lichen Moth, Miltochrista calamine, and Its Diastereomer

Synlett ◽  
2021 ◽  
Author(s):  
Jiangchun Zhong ◽  
Gucheng Yuan ◽  
Jiawei Liu ◽  
Shihang Yu ◽  
Xueyang Wang ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Enantioselective Synthesis ◽  
Synthetic Approach ◽  
Chiral Auxiliaries ◽  
Synthetic Sex Pheromone ◽  
Key Steps

AbstractThe synthesis of a Miltochrista calamine sex pheromone and its diastereomer has been developed. The key steps of the synthetic approach involved Evans’ chiral auxiliaries and the addition of alkyne to aldehyde, which were firstly applied to prepare this sex pheromone and its diastereomer. The synthetic sex pheromone could be used to trap insects and study physiological and ecological questions of the lichen moth.

A Concise Enantioselective Synthesis of (S)-Preclamol via Asymmetric Catalytic Negishi Cross-Coupling Reaction

Synlett ◽  
2019 ◽  
Vol 30 (07) ◽  
pp. 860-862 ◽  
Author(s):  
Yun Zhou ◽  
Chunxiao Liu ◽  
Lifeng Wang ◽  
Leng Han ◽  
Shicong Hou ◽  
...  
Keyword(s):  
Total Yield ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Synthetic Approach ◽  
Chiral Drugs ◽  
Asymmetric Catalytic ◽  
Cross Coupling Reaction ◽  
Tertiary Carbon ◽  
Key Steps

A novel, concise, and efficient enantioselective synthesis of (S)-preclamol (87% ee, 51% total yield) has been developed. The key steps of this synthetic approach included cobalt-catalyzed asymmetric catalytic cross-coupling of α-bromo ester with arylzinc and the reduction of chiral ester to diol with a tertiary carbon atom. Moreover, it was demonstrated that our enantioselective Negishi cross-coupling was a powerful tool to construct stereogenic benzylmethyl center in chiral drugs on a gram scale.

scholarly journals An enantioselective synthesis of the C24–C40 fragment of (−)-pulvomycin

2014 ◽  
Vol 50 (38) ◽  
pp. 4901-4903 ◽  
Author(s):  
Sandra Börding ◽  
Thorsten Bach
Keyword(s):  
Synthesis Method ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Pure Form ◽  
Enantiomerically Pure ◽  
Diastereoselective Addition ◽  
Key Steps

The C24–C40 fragment of (−)-pulvomycin was prepared in enantiomerically pure form using a concise synthesis method (15 linear steps from d-fucose, 6.8% overall yield) featuring a diastereoselective addition to an aldehyde, a β-selective glycosylation and a Stille cross-coupling as the key steps.

Synthesis of enantiomerically pure (S)-(+)-3-hydroxytetrahydrofuran, and its (R)-enantiomer, from malic or tartaric acid

1983 ◽  
Vol 48 (16) ◽  
pp. 2767-2769 ◽  
Author(s):  
Vishnu K. Tandon ◽  
Albert M. Van Leusen ◽  
Hans Wynberg
Keyword(s):  
Tartaric Acid ◽  
Enantiomerically Pure

Synthesis of enantiomerically pure macrolides with hydrazide fragments from tetrahydropyran and l-(+)-tartaric acid derivatives

2013 ◽  
Vol 62 (1) ◽  
pp. 217-219 ◽  
Author(s):  
G. Yu. Ishmuratov ◽  
M. P. Yakovleva ◽  
G. R. Mingaleeva ◽  
M. A. Shutova ◽  
R. R. Muslukhov ◽  
...  
Keyword(s):  
Tartaric Acid ◽  
Enantiomerically Pure ◽  
Tartaric Acid Derivatives

Total Synthesis of Bis-anthraquinone Antibiotic BE-43472B

Synthesis ◽  
2018 ◽  
Vol 50 (13) ◽  
pp. 2490-2515 ◽  
Author(s):  
Yu Yamashita ◽  
Yoichi Hirano ◽  
Akiomi Takada ◽  
Hiroshi Takikawa ◽  
Keisuke Suzuki
Keyword(s):  
Total Synthesis ◽  
Hydroxy Group ◽  
Three Dimensional ◽  
Crystal Structure Analysis ◽  
Aryl Group ◽  
Full Account ◽  
Ring Fusion ◽  
Enantiomerically Pure ◽  
Pinacol Rearrangement ◽  
Key Steps

This is a full account of our synthetic endeavor on the total synthesis of bis-anthraquinone antibiotic BE-43472B, an unusual octacyclic aromatic polyketide with a bis-anthraquinone scaffold. Three key steps enabled a facile access to the anthraquinone unit corresponding to the ABCF rings; (1) cyclo-condensation or -addition of benzonitrile oxides with cyclic enone derivatives, (2) benzoin cyclization for the stereoselective ring fusion with an angular hydroxy group, and (3) pinacol rearrangement for stereoselective installation of the angular aryl group. Other keys for the success include, (4) diastereoselective methylation of a lactol derivative, and (5) late-stage installation of the C3 hydroxy group through stereoselective oxirane ring formation via halohydrin derivatives. Whereas oxidation of the double bond in the enone with an adjacent 1,3-diketone moiety failed, the projected oxidation was achieved with the alkene keeping the isoxazole moiety intact as a 1,3-diketone equivalent. In the racemic total synthesis, X-ray crystal structure analysis of the target was achieved, proving the three-dimensional architecture for the first time. The asymmetric total synthesis was also achieved by exploiting a cycloadduct of the nitrile oxide and the enantiomerically pure cyclohexenone, which was convertible to the common intermediate via dehydrogenation followed by alkoxycarbonylation.

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