83698-29-7Relevant academic research and scientific papers
Total synthesis of (-)-ophiodilactone A and (-)-ophiodilactone B
Matsubara, Takaaki,Takahashi, Keisuke,Ishihara, Jun,Hatakeyama, Susumi
, p. 757 - 760 (2014/01/23)
The first asymmetric total synthesis of (-)-ophiodilactone A and (-)-ophiodilactone B, isolated from the ophiuroid (Ophiocoma scolopendrina), is reported. The key features of the synthesis include the highly stereocontrolled construction of the structurally congested γ-lactone/δ-lactone skeleton through an asymmetric epoxidation, diastereoselective iodolactonization, and intramolecular epoxide-opening with a carboxylic acid, and biomimetic radical cyclization of ophiodilactone A to ophiodilactone B. Bioinspired synthesis: The first total synthesis of the title compounds has been accomplished in a highly stereocontrolled manner. Key features of the synthesis include an asymmetric epoxidation, a diastereoselective iodolactonization, an intramolecular epoxide opening with a carboxylic acid, and a biomimetic radical cyclization of ophiodilactone A to ophiodilactone B. Copyright
Stereoselective synthesis of the fused γ-lactone/ δ-lactone core of ophiodilactones
Matsubara, Takaaki,Takahashi, Keisuke,Ishihara, Jun,Hatakeyama, Susumi
, p. 155 - 158 (2013/08/23)
A promising precursor of ophiodilactones A and B, tetrameric phenyl propanoids isolated form the ophiuroid Ophiocoma scolopendrina, has been synthesized stereoselectively employing a halolactonization and an intramolecular epoxide-opening with a carboxyli
Transformation of Alkyl Halides to Aldehydes Having Two Additional Carbon Atoms
Shankaran, K.,Talekar, D. G.,Rao, A. S.
, p. 408 - 410 (2007/10/02)
Methyl 3-oxo-4-phenylbutanoate (6) reacts with alkyl halides (1a-g) in the presence of NaH/benzene to furnish alkylated β-keto esters (2a-g).Hydrolysis of 2a-g gives benzyl ketones (3a-g), which on reduction with sodium borohydride give the homobenzylic alcohols (4a-g).The alcohols (4a-g) are readily fragmented to aldehydes (5a-g) on heating with lead tetraacetate/iodine.
