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1.
Chem Pharm Bull (Tokyo) ; 64(10): 1474-1483, 2016 Oct 01.
Article in English | MEDLINE | ID: mdl-27452927

ABSTRACT

We have developed a new method for synthesizing chiral isotwistane and homoisotwistane skeletons as well as aminocyclitols in a highly stereoselective manner. These results were achieved through the use of a common intermediate, which was derived from the ytterbium-catalyzed asymmetric Diels-Alder reaction of Danishefsky diene.


Subject(s)
Alkanes/chemical synthesis , Bridged-Ring Compounds/chemical synthesis , Cyclitols/chemical synthesis , Cyclohexenes/chemistry , Alkanes/chemistry , Bridged-Ring Compounds/chemistry , Catalysis , Cyclitols/chemistry , Cycloaddition Reaction , Molecular Structure , Stereoisomerism , Ytterbium/chemistry
2.
J Org Chem ; 75(11): 3871-4, 2010 Jun 04.
Article in English | MEDLINE | ID: mdl-20459138

ABSTRACT

The catalytic asymmetric total synthesis of platyphyllide has been accomplished. A key highly substituted cyclohexene derivative has been obtained by the catalytic asymmetric Diels-Alder reaction of Danishefsky diene with an electron-deficient alkene. The Diels-Alder adduct was converted to a protected cyclohexane-1,3-dione in chiral form by catalytic Ito-Saegusa oxidation. Although the reported structure of platyphyllide was successfully synthesized, the optical rotation was opposite that of the natural compound. The absolute configuration of natural (-)-platyphyllide is revised to be a (6S,7S)-enantiomer.


Subject(s)
Cyclohexenes/chemistry , Cyclohexenes/chemical synthesis , Alkenes/chemistry , Benzofurans , Catalysis , Cyclohexanes , Ketones , Molecular Structure , Optical Rotation , Stereoisomerism
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