KOBAYASHI Kazuhiro Hokkaido Univ., Fac.of Eng., Instructor, 工学部, 助手 (90161976)
ORITO Kazuhiko Hokkaido Univ., Fac.of Eng., Instructor, 工学部, 助手 (20109482)
TOKUDA Masao Hokkaido Univ., Fac.of Eng., Assoc.Professor, 工学部, 助教授 (80001296)
|Budget Amount *help
¥7,200,000 (Direct Cost : ¥7,200,000)
Fiscal Year 1990 : ¥1,300,000 (Direct Cost : ¥1,300,000)
Fiscal Year 1989 : ¥5,900,000 (Direct Cost : ¥5,900,000)
1. New Synthesis of macrolides based on beta-scission of alkoxyl radicals. A simple new method was devised for the synthesis of macrolides based on a consecutive intramolecular homolytic addition-bata-scission of alkoxyl radicals. 11 to 16-Membered macrocyclic lactones including ((〕SY.+-.〔))-recifeiolide have been efficiently prepared by this new method.
2. New method for the transformation of steroids into physiologically-active 18- or 19- norsteroids based on bata-scission of alkoxyl radicals New method for transformation of steroids into 18- and 19-norsteroids and ring-A- aromatized steroids was devised. Several physiologically-active 18-, and 19-norsteroids were synthesized by this method.
3. Synthesis of heterocyclic quinones based on a new [2+3] photoaddition. A one-step formation of 2,3-dihydronaphto[2,3-b]furan-4,9-diones by a new [2+3] type regioselective photoaddition of 2-hydroxy-1,4-naphthoquinones with a variety of alkenes wa13EA\ : s devised. The dihydronaphthofurandiones were readily transformed into naphtho[2,3-b]furan-4,9-diones including a natural quinone, maturinone. Efficient one-step synthesis of 2,3-dihydro-1H- benz[f]indole-4,9-diones of 1H-benz[f]indole-4,9-diones ba13EA\ : sed on an unprecedented 2+3 type regioselective photoaddition of 2-aminoquinone with various alkenes was also devised.
4. New synthesis of physiologically-active heterosteroids. A new method was devised for transforming steroidal cyclic ketones into steroidal cyclic amines, cyclic sulfies, cyclic tellurides, and cyclic selenides with the same ring size via 5 to 6 st13EA\ : eps. A number of heterosteroids were synthesized by this method.
5. Other Results stereoselective synthesis of 2,5-disubstituted pyrrolidines by anodic oxidation of delta-alkenylamines, new method for remote functionalization, new synthesis of lignanes, and new method for the annelatioin etc. were devised.