20 Δ^<9(12)>-カプネレン-8β,10α-ジオール及び、Δ^<9(12)>-カプネレン-3β,8β,10α-トリオールの全合成
スポンサーリンク
概要
- 論文の詳細を見る
The first achievement of total syntheses of two marine sesquiterpenes, (±)-Δ^<9(12)>-capnellene-8β,10α-diol(1) and (±)-Δ^<9(12)>-capnellene-3β,8β,10α-triol(3) will be disclosed. In the first place the efficient syntheses of the two key intermediate 16 and 21 corresponding to the AB-rings of the two sesquiterpenes will be presented. The synthesis utilized the common intermediate 12 easily produced from the silyl enol ether 10 by Saegusa-Ito reaction. Interestingly treatment of 12 with DBU in refluxing benzene gave 13 exclusively. In the second place the construction of the ABC-ring corresponding to 1 will be discussed. As expected, the aldol condensation of 23 under a variety of the reaction conditions provided only a trace amount of the desired product. However, this difficulty was nicely overcome by utilizing organosilicon chemistry. Namely treatment of 23 with TMSOTf-NEt_3 in refluxing benzene gave the desired product 24 in 40% yield together with the recovery of 23 30%. In the third place accomplishment of (±)-Δ^<9(12)>-capnellene-8β,10α-diol(1) via the triol 31 will be presented. In contrast to the triol route the allylsilane route shown in schemeV provided the stereoisomer 29, whose x-ray analysis is now under way. In the last place, according to the reaction sequence developed in the total synthesis of(±)-1, transformation of 21 to (±)-Δ^<9(12)>-capnellene-3β,8β,10α-triol(3) will be discussed.
- 天然有機化合物討論会の論文
- 1985-09-07
著者
-
柴崎 正勝
Faculty Of Pharmaceutical Sciences Teikyo University:(present Address)faculty Of Pharmacertical Scie
-
池上 四郎
帝京大学薬学部
-
間瀬 俊明
Sagami Chemical Research Center
-
柴崎 正勝
相模中研
-
間瀬 俊明
相模中研
-
池上 四郎
帝京大薬
-
池上 四郎
Faculty Of Pharmaceutical Sciences Teikyo University
-
池上 四郎
帝京大 薬
関連論文
- 温度応答性高分子触媒を用いる環境調和型酸化反応システムの開発
- ヒト動脈硬化病巣表層部を認識するモノクロナル抗体の抗原解析
- AN EXTREMELY MILD AND GENERAL METHOD FOR THE CONSTRUCTION OF 1,2-TRANS-β-GLYCOSIDIC LINKAGES VIA GLYCOPYRANOSYL DIETHYL PHOSPHITES WITH PARTICIPATING GROUPS AT C-2
- 含リン脱離基を基盤とする高選択的グリコシル化反応
- プロスタグランジンの合成と医薬 (脂質の化学と生化学) -- (脂質の生化学)
- グリコシル化反応の新展開
- AN EFFICIENT CONSTRUCTION OF 1,2-TRANS-β-GLYCOSIDIC LINKAGES VIA BENZYL-PROTECTED GLYCOPYRANOSYL P, P-DIPHENYL-N-(p-TOLUENESULFONYL)-PHOSPHINIMIDATES
- 17β-HYDROXY-16α-[^I]IODOWORTMANNIN, A SENSITIVE LABELING AGENT FOR PI 3-KINASES
- 21世紀薬学と製薬産業長期ビジョン : これからの産学協調を模索して
- 4-Allyl-2-azetidinone と Penicillium simplicissimum による土壌伝染性フザリウム病の発病抑制
- A NOVEL HOMOISOCARBACYCLIN ANALOG WITH POTENT AND LONG-LASTING ACTIVITY
- SYNTHESIS OF CIS-BICYCLO[4.3.0]NON-2-ENE DERIVATIVES. : THE POTENT HOMOISOCARBACYCLIN ANALOGS
- SYNTHESIS OF 11-DEOXO-11-METHYLENE-PROSTAGLANDIN D_2 AND ITS DERIVATIVES
- 功労賞受賞 池川信夫氏の業績
- 創薬科学賞受賞 Rhoキナーゼ阻害剤エリルの創薬(紹介)
- 奨励賞受賞 高橋秀依氏の業績
- 池上四郎会頭に聞く
- 糖と創薬研究
- 功労賞受賞山崎幹夫氏の業績
- 日本の化学系学術情報誌の将来を考える
- AIMECS 95 : AFMC(アジア医薬化学連合), 国際医療化学シンポジウム
- 薬学会年会における広報活動
- A Total Synthesis of (+)-Hirsutic Acid
- 薬学教育に不可欠な有機化学(薬学教育のあり方)
- 創薬科学を構想する
- 日本薬学会功労賞受賞 持田英氏の業績
- Efficient Synthesis of Isocarbacyclins
- Studies on Topical Antiinflammatory Corticosteroids. III. : Synthesis and Vasoconstrictive Activity of 11β, 17α, 21-Trihydroxy-2'-phenyl-2'H-2,4-pregnadieno[3,2-c]pyrazol-20-one Derivatives
- Studies on Topical Antiinflammatory Corticosteroids. II. : Synthesis and Vasoconstrictive Activity of 11β, 17α, 21-Trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione 17-Methoxy- and (Methylthio)acetates
- Studies on Topical Antiinflammatory Corticosteroids. I. Syntheses and Vasoconstrictive Activities of 11β, 17α, 21-Trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione 17-Ester and 17,21-Diester Derivatives
- Asymmetric Heck-Type Reaction Utilizing Hypervalent Alkenyliodonium Salt
- Stereochemical Studies. XXIII. Stereochemistry of the Thermal Isocyanide-Cyanide Rearrangement
- 21世紀薬学に向って
- Alkylated Levoglucosan in Organic Synthesis. : A Formal Total Synthesis of Elaiophylin
- The Effects of Neighboring Heteroatoms in Ring Opening of Epoxides
- Stereochemical Studies. XXXIX. A Novel Method for the Preparation of Optically Active Aldehydes. Syntheses of Optically Active (R) (+)-α-Cyclocitral, (S) (+)-Dehydrovomifoliol, and (S) (+)-Abscisic Acid
- Stereochemical Studies. XXXV. A Biogenetic-type Asymmetric Cyclization. Syntheses of optically Active α-Cyclocitral and trans-α-Damascone
- Stereochemical Studies. XXXIV. A Novel Biogenetic-type Cyclization of Citral to α-Cyclocitral via an Enamine
- 中国製ダイエット用健康食品中のN-nitrosofenfluramineの光学純度の決定
- SYNTHESIS OF A NEW CHEMICALLY STABLE PROSTACYCLIN ANALOGUE WITH HIGH AND LONG-LASTING ACTIVITY
- A Formal Total Synthesis of Thienamycin from 4-Propargyl-2-azetidinone
- 4-Propargyl-2-azetidinone as a Versatile Synthon for the Synthesis of β-Lactam Antibiotics : Hydrostannation and Its Reactivities
- 20 Δ^-カプネレン-8β,10α-ジオール及び、Δ^-カプネレン-3β,8β,10α-トリオールの全合成
- Synthesis of dl-9 (O)-Methano-△^6-prostaglandin I_1
- 43 Δ^-Capnellene-3β,8β,10α-triolの合成研究
- Novel Reactivities on tert-Butyldimethylsilyl and tert-Butyldiphenylsilyl Ethers : Application to the Synthesis of 11-epi-PGF_
- 8 (+)-ヒルスチン酸の高選択的全合成
- キレ-ション制御による高選択的反応--天然物合成への利用
- 25 (±)-Coriolinの全合成
- 新しいプロスタグランジンおよびその類縁体の合成と生理活性 (「医薬品開発をめぐる生理活性物質の合成」特集号)
- Lactams. VI. Synthesis and Nuclear Magnetic Resonance Study of 1-Aralkyl-3-methyl- and -5-methyl-2(1H)-pyridones
- 21世紀薬学像を探る
- The Roles of Hetero Atoms in Solvolytic Reactions. III. Some Evidence for Preference of Intramolecular Catalysis by Nitrogen in Hydrolysis of Tertiary Alkyl Esters
- 69 ビニロキシボラン-イミン縮合反応を利用した有用生理活性天然物の合成研究
- Stereochemical Studies. XXI. Studies on α-Alkyl-α-amino Acids. XV. Application of Thermal Isocyanide-Cyanide Rearrangement to R-S Conversion of α-Methylphenylalanine
- A Synthesis of ^C-Labeled Sodium 2-[o-[(2,6-Dichlorophenyl)-amino] phenyl] acetate ([^C] Diclofenac Sodium)
- Synthesis of dl-9 (O)-Methanoprostaglandin-I_1
- A Simple and Efficient Conversion of Aldehyde Acetals into Esters
- A New Efficient Method for Conversion of Corticosteroid 17α, 21-Cyclic Ortho Esters to 17α-Acyloxy-21-chloro-21-deoxy Derivatives
- Quinolizidines. I. : Quaternization of the Quinolizidine System : Effect of β, γ-Unsaturation on Stereoselectivity in Methiodide Formation
- Chemistry of Diborane and Sodium Borohydride. VI. The Reaction of Amides with Sodium Borohydride
- Chemistry of Sodium Borohydride and Diborane. II. Reduction of Schiff Bases with Diborane in Tetrahydrofuran
- Chemistry of Sodium Borohydride and Diborane.I. Some New-type of Amine Boranes
- Synthesis of the Heterocyclic Compounds by Pschorr Cyclization. III. Syntheses of 10,11-Methylenedioxy-7,8-dihydro-6H-benzo[c]pyrid-[1,2-a]azepinium Salts and Their Derivatives
- Reduction of Acid Amides to Amines with Sodium Borohydride
- Neosaccharide--新しいエーテル結合糖の設計と合成 (特集/期待される生体機能分子の実用化)
- オルトエステル糖の合成, 構造, およびその応用
- Pd(II)を用いた触媒的Ferrier環化反応の開発とその生物活性物質合成への応用
- 薬学会賞受賞 橋本俊一氏の業績
- 多方面の研究に興味を抱いて
- 有機合成と創薬 : PG類縁体
- 医薬品の配列と化学名(12局へ望むもの)
- 役員選出制度を考える(日本薬学会役員選出制度の問題点)
- 偏りのない推薦と選考方式を(日本薬学会賞技術賞[仮称]に対する希望)
- 化合物命名のための本
- キレーション制御による高選択的反応 : 天然物合成への利用
- 真空ポンプ
- 新しいプロスタグランジンおよびその類縁体の合成と生理活性
- タイトル無し
- タイトル無し