TY - JOUR
T1 - Synthesis of Natural Products Containing Cyclohexane Units Starting from Aldohexoses
AU - Chida, Noritaka
AU - Ogawa, Seiichiro
PY - 1995
Y1 - 1995
N2 - Preparation of optically active, highly functionalized carbocycles is an important issue in recent synthetic organic chemistry. Ferrier's carbocyclization reaction, which provides optically pure cyclohexanones from aldohexoses, is one of the most efficient procedures for this purpose. Chiral and highly oxygenated cyclohexanes obtained by this reaction are potentially versatile chiral building blocks in natural product synthesis. In this article, the development of catalytic Ferrier's carbocyclization reaction with mercury (II) trifluoroacetate, and total syntheses of natural products containing cyclohexane units (hygromycin A, lycoricidine, and mesembranol) starting from aldohexoses using this reaction as the key steps are described The methodology described in this article extends the usefulness of carbohydrates as chiral building blocks to the synthesis of natural products possessing cyclohexane rings in optically active forms.
AB - Preparation of optically active, highly functionalized carbocycles is an important issue in recent synthetic organic chemistry. Ferrier's carbocyclization reaction, which provides optically pure cyclohexanones from aldohexoses, is one of the most efficient procedures for this purpose. Chiral and highly oxygenated cyclohexanes obtained by this reaction are potentially versatile chiral building blocks in natural product synthesis. In this article, the development of catalytic Ferrier's carbocyclization reaction with mercury (II) trifluoroacetate, and total syntheses of natural products containing cyclohexane units (hygromycin A, lycoricidine, and mesembranol) starting from aldohexoses using this reaction as the key steps are described The methodology described in this article extends the usefulness of carbohydrates as chiral building blocks to the synthesis of natural products possessing cyclohexane rings in optically active forms.
KW - Aldohexoses
KW - Carbohydrates
KW - Chiral building block
KW - Ferrier's carbocyclization reaction
KW - Functionalized carbocycles
KW - Hygromycin A
KW - Lycoricidine
KW - Mesembranol
KW - Natural product synthesis
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U2 - 10.5059/yukigoseikyokaishi.53.858
DO - 10.5059/yukigoseikyokaishi.53.858
M3 - Article
AN - SCOPUS:0029387715
VL - 53
SP - 858
EP - 868
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
SN - 0037-9980
IS - 10
ER -