1 Clerodin類縁体の合成研究2 : 構造と生物活性相関の合成的研究
スポンサーリンク
概要
- 論文の詳細を見る
I. 1.1-t-Butyl-7-hydroxy perhydrofuro [2,3-b] furan 1 which was selected asamodel compound about the antifeeding active center of the neo-clerodane diterpenes and that was synthesized via a furan-alcohol which was derived by a coupling reaction with an epoxide and Li di(3-furyl)cuprate. Although 1 of diastereomeric mixture could not separated on TLC etc., its lactone derivative gave lactone a and b as a fine crystal. Configurations of their H^1 protons could not determined from the nmr spectra, since their coupling constants had approximately the same values to each others. Then we decided successfully the configuration of the protons and the conformation of the compounds by the combination of the LIS experiments (LIS) and the empirical force-field calculation (EFF). I. 2. We reported that the synthesis of the clerodin homologue 3 for investigation of the structure-activity relationship. However, it was very difficult to determine the C^<11> configuration on the epoxy-acetonide 8 of the synthetic intermediate. Thus, we synthesized the diastereomeric hydroxy-acetonide A (9) and B (10) via an epoxidation reaction by mCPBA or NBS. Each C^<11> configuration of the derivatives was determined by the EFF-LIS combination method, as well as lactone a and b, as shown in Fig. 2. II. Mono and disubstituted benzene derivatives were synthesized for clarifing the stabilization of the perhydrofuro[2,3-b]furan ring by steric effect. It is noteworthy that the furo-furan derivative from sym-m-xylenol detected as a 1: 1 mixture of 4 and 11+12 on NMR, whereas ca. 90% amounts of dimethyl benzene derivative 18 existed in the perhydrofuro[2,3-b]furan ring form.
- 天然有機化合物討論会の論文
- 1980-09-10
著者
関連論文
- B26 ニガウリのウリミバエ誘引物質(フェロモン・行動制御)
- 233 ニガウリ果実に存在するウリミバエ誘引物質
- ミカンハダニのベンゾメート抵抗性 : II. ^3H-ベンゾメートの表皮透過性と代謝
- 44(PA1-2) ゴキブリの性フェロモン、ペリプラノンAに関連したゲルマクレンDの生合成類似反応(ポスター発表の部)
- 89 シトレオビリジノール及び関連代謝産物の構造及び合成
- 3 Teucrin P1の立体配座解析 : 単離可能な安定及び不安定立体配座異性体の構造解析
- ペルヒドロフロ〔2,3-b〕フラン環系昆虫摂食阻害物質におけるフロフラン環の立体制御と生物活性 (生物活性物質)
- Anodic Oxidation of 4-Hydroxycinnamic Acids and Related Phenols
- Anodic Oxidation of Some Propenylphenols : Synthesis of Physiologically active Neolignans
- Anodic Oxidation of 4-Allyl-2,6-dimethoxyphenol and Related Compounds : Syntheses of Asatone and Related Neolignans
- 41 生理活性ネオリグナンの分離・構造およびその電解合成
- 6 Clerodane diterpene化合物の絶対配置について : X線解析及びCDスペフトルの矛盾する結果に対する立体配座からの解明
- 51 細辛のネオリグナン
- 76 細胞融合の手法による新しいハイブリッド菌株とその新規代謝産物(口頭発表の部)
- 30 クサギ葉中の昆虫忌避性物質Clerodendrin AおよびBの構造
- 13 ゲルマクレン型セスキテルペンの生合成類似反応
- 1 Clerodin類縁体の合成研究2 : 構造と生物活性相関の合成的研究
- 14 Clerodin類縁体の合成研究 : 構造と生物活性相関の合成的研究