Marine Terpenes and Terpenoids. X. : Acid-Catalyzed Transannular Cyclization of 11,12-Epoxy-cembranolide

スポンサーリンク

概要

• 論文の詳細を見る

• Acid-catalyzed transannular cyclization of 11,12-epoxycembranolide (1), isolated from the soft coral Sinularia mayi, was studied. The major product was the trans-fused bicyclo[8.4.0]tetradecene derivative 2,and the maximum yield was 89% with boron trifluoride in benzane at 0℃. When treated with p-toluenesulfonic acid in benzene at 55℃, 1 gave a bicyclo[9.3.0]tetradecene derivative 11 in 36% yield. Its immediate precursor was shown to be the allylic alcohol 4,which was converted to 11 on treatment with p-toluenesulfonic acid. The stereochemistries of the cyclization products indicated that the reaction takes place throught a conformation in which the dispositions of 11,12- and 12,13-bonds are crossed, with respect to the 7,8- and 3,4-double bonds, respectively.

• 社団法人日本薬学会の論文
• 1990-03-25

著者

• 濱口 卓也

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 小林 優

  Faculty Of Pharmaceutical Sciencces Hokkaido University

• 小林 優

  北大薬

関連論文

• P-6 Fucofuranoside法 : β-D-およびβ-L-fucofuranoside誘導体でのpyridine-induced shift差による二級水酸基の絶対配置の決定法(ポスター発表の部)
• Marine Sterols. XI. Polyhydroxysterols of the Soft Coral Sarcophyton glaucum : Isolation and Synthesis of 5α-Cholestane-1β, 3β, 5,6β-tetrol
• Isolation of 23-Methylcholesta-5,22-dien-3β-ol from the Soft Coral Sarcophyton glaucum
• 88(P19) カイラルな3級アルコールへのフコフラノサイド法の適用(ポスター発表の部)
• P-5 ポリハイドロキシステロイドの^C NMRの加成則について(ポスター発表の部)
• 78 軟サンゴ、Sinularia mayiおよびLobohytum strictumから得られたステロイドとセンブラノイドの構造(ポスター発表の部)
• 57 アンダマン、ニコバー産の軟サンゴ、スポンジ、紅藻から得られたステロイドの構造(ポスター発表の部)
• Marine Sterols. XIX. Polyhydroxysterols of the Soft Corals of the Andaman and Nicobar Coasts. (3). Isolation and Structures of Five New C_ Polyhydroxysterols from Two Sclerophytum sp. Soft Corals
• 20 オオイソバナ(gorgonian coral)と数種の軟サンゴからのpolyhydroxysterol類の構造(ポスター発表の部)
• Marine Sterols. XVII. : Polyhydroxysterols of the Soft Corals of the Andaman and Nicobar Coasts. : (2). Isolation and Structures of Three 16β-Hydroxy Steroidal Glycosides from an Alcyonium sp. Soft Coral
• Marine Sterols. XVI. : Polyhydroxysterols of the Soft Corals of the Andaman and Nicobar Coasts. (1). : Isolation of (24S)-24-Methylcholest-5-ene-3β, 25ζ, 26-triol and (24S)-24-Methylcholestane-3β, 5β, 6α, 25-tetrol
• 71(P2-1) 軟サンゴ、オオウミキノコからの新センブラン型ジテルペン類の構造と分子内閉環反応(ポスター発表の部)
• Marine Terpenes and Terpeoids. IX. : Structures of Six New Cembranoids, Sarcophytols F, K, P, Q, R and S, from the Soft Coral Sarcophyton glaucum
• Marine Terpenes and Terpenoids. VIII. : Transannular Cyclization of 3,4-Epoxy-1,7,11-cembratriene Systems
• Marine Terpenes and Terpenoids.VII. : Minor Cembranoid Derivatives, Structurally Related to the Potent Anti-tumor-Promoter Sarcophytol A, from the Soft Coral Sarcophyton glaucum
• 28 軟サンゴ、オオウミキノコからの新センブラン型ジテルペンの構造(口頭発表の部)
• 10-Hydroxypheophytins and a New Norlabdane Diterpene from the Leaves of Cupressus funebris ENDL.
• Studies on the Constituents of Umbelliferae Plants. XVIII. : Minor Constituents of Bupleuri Radix : Occurrence of Saikogenins, Polyhydroxysterols, a Trihydroxy C_ Fatty Acid, a Lignan and a New Chromone
• Marine Terpenes and Terpenoids. V. : Oxidation of Sarcophytol A, a Potent Anti-tumor-Promoter from the Soft Coral Sarcophyton glaucum
• Studies on the Constituents of Umbelliferae Plants. XVII. Structures of Three New Ligustilide Derivatives from Ligusticum wallichii(Organic,Chemical)
• Marine Terpenes and Terpenoids. III. Isolation and Structures of Two Cembrane Diols from the Soft Coral Sinulana mayi(Organic,Chemical)
• Studies on the Constituents of Umbelliferae Plants. XV. Constituents of Cnidium officinale : Occurrence of Pregnenolone, Coniferylferulate and Hydroxyphthalides(Organic,Chemical)
• Marine Sterols. XV. Isolation of 24-Vinyloxycholesta-5,23-dien-3β-ol from the Brown Alga Sargassum thumbergii
• COMPONENTS OF CNIDIUM OFFICINALE MAKINO : OCCURRENCE OF PREGNENOLONE, CONIFERYL FERULATE, AND HYDROXYPHTHALIDES
• Marine Sterols. XIV. Isolation of (24S)-24-Methyl-5α-cholestane-3β, 5,6β, 25ζ, 26-pentol from the Soft Coral Sarcophyton glaucum
• ISOLATION OF 5α, 6-DIHYDROGLAUCASTEROL, A NEW MARINE C_ STEROL WITH A 24,26-CYCLIZED SIDE CHAIN, FROM THE SOFT CORAL SARCOPHYTON GLAUCUM
• Marine Terpenes and Terpenoids. I. Structures of Four Cembrane-type Diterpenes : SarCophytol-A, Sarcophytol-A Acetate Sarcophytol-B, and Sarcophytonin-A, from the Soft Coral, Sarcophyton glaucum
• Marine Sterols. III. Synthesis of Asterosterol, a Novel C_ Sterol from Asteroids
• Marine Terpenes and Terpenoids. X. : Acid-Catalyzed Transannular Cyclization of 11,12-Epoxy-cembranolide
• Marine Terpenes and Terpenoids. VI. : Isolation of Several Plausible Precursors of Marine Combranolides : from the Soft Coral, Sinularia mayi
• Marine Terpenes and Terpenoids. II. Structures of Three Cembrane-type Diterpenes, Sarcophytol-C, Sarcophytol-D, and Sarcophytol-E, from the Soft Coral, Sarcophyton glaucun Q. et. G
• Polyphosphoric Acid-catalyzed Beckmann Rearrangement of 3-Keto-steroid Oximes
• Marine Sterols. XXIV. Isolation of 24-Methylenecholestane-1α, 3β, 3α, 6β, 16β-pentol from Sinularia sp. of Soft Coral
• Marine Sterol. XXV.Isolation of 23-Demethylgorgost-7-ene-3β, 5α, 6β-triol and(24S)-Ergostane-3β, 5α, 6β, 7β, 15β-pentol from Soft Corals of the Andaman and Nicobar Coasts
• Marine Terpenes and Terpenoids. XIV. Absolute Configuration and Acid-Catalyzed Transformation of (-)-12,13-Didehydrofurospongin-1 Isolated from an Arabian Sea Sponge, Fasciospongia cavernosa SCHMIDT
• Marine Sterols. XXI. Isolation of (24S)-3β-Hydroxyergost-5-en-21-oic Acid form a Sclerophytum sp. of Soft Coral
• Marine Sterols. XXII. Occurrence of 3-Oxo-4,6,8(14)-triunsaturated Steroids in the Sponge Dvsidea herbacea
• Marine Terpenes and Terpenoids. XIII. Isolation of a New Dihydrofuranocembranoid, Sarcophytonin E, from the Sarcophyton sp. Soft Coral of Okinawa
• Marine Terpenes and Terpenoids. XI. : Structures of New Dihydrofuranocembranoids Isolated from a Sarcophyton sp. Soft Coral of Okinawa
• CONFORMATIONAL STUDY OF THE CEMBRANOID SARCOPHYTOL A, A POTENT ANTI-TUMOR-PROMOTER
• Marine Terpenes and Terpenoids. IV. Isolation of New Cembranoid and Secocembranoid Lactones from the Soft Coral Sinularia mayi
• Studies on the Constituents of Umbelliferae Plants. XVI. Isolation and Structures of Three New Ligustilide Derivatives from Angelica acutiloba(Organic,Chemical)
• Apparent Lack of Tetrodotoxin Biosynthesis in Captured Taricha torosa and Taricha granulosa
• 21 ヒトデ類のステロールの研究
• Reaction of Some Steroidal Amides and Unsaturated Lactams with Nitrous Acid
• Marine Sterols. I. Sterols of Annelida, Pseudopotamilla occelata MOORE
• Polyphosphoric Acid-catalyzed Beckmann Rearrangement of 4-Methylcholest-4-en-3-one Oxime
• Reaction Products of 4-Aza- and 4-Methyl-4-azacholest-5-en-3-one with Nitrous Acid

もっと見る 閉じる

スポンサーリンク