1991 Fiscal Year Final Research Report Summary
Novel Ring Transformation Reaction
| Project/Area Number |
02453142
|
|---|
| Research Category |
Grant-in-Aid for General Scientific Research (B)
|
| Allocation Type | Single-year Grants |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | Kyushu University |
|---|
Principal Investigator |
SAKAI Kiyoshi Kyushu Univ., Pharmaceutical Sciences, Professor, 薬学部, 教授 (90153840)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
SUEMUNE Hiroshi Kyushu Univ., Pharmaceutical Sciences, Assistant Professor, 薬学部, 助手 (20095897)
FUNAKOSHI Kazuhisa Kyushu Univ., Pharmaceutical Sciences, Associate Professor, 薬学部, 助教授 (50037579)
|
|---|
| Project Period (FY) |
1990 – 1991
|
| Keywords | ring transformation / aldol condensation / acetalization / Grob fragmentation / boron trifluoride / ring cleavage / ethylene glycol |
|---|
| Research Abstract |
A novel ring transformation reaction based on aldol condensation followed by acetafization and subsequent Grob fragmentation has been developed by our group. This reaction takes place when the cychc ketones with a carbonyl function at the side chain are subjected to acetatization using BF_3/ethylene glycol in CH_2Cl_2 at room temperature. This facile ring transformation can be classified into two types. One is the intramolecular ring transformation, and the other is the intermolecular ring transformation. The intramolecular ring transformation reaction has been successfully applied for the synthesis of natural products such as bulnesol, acorenone B, trichodiene, and phoracantholide 1. The reaction based on intermolecular aldol condensation has provided a novel synthetic route to chiral straight-chain compounds with syndiotactic methyl function. Ring transformation from readily prepared bicycle[3.3.0]octan-3-ones to bicycle[3.2.1]oct-2-ones is now extended to a study of asymmetric ring transformation.
|
