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Showing papers by "Leo A. Paquette published in 1987"



Journal ArticleDOI
TL;DR: The title compound (3), a molecule whose central cyclobutane ring is 1,3-bonded in hybrid fashion to two butadiene units, has been prepared and its thermal stability assessed relative to 1 and 2 as mentioned in this paper.

18 citations


Book
01 Jan 1987
TL;DR: In this paper, the authors present an analysis of the theoretical and physical properties of polyquinane compounds, including the reaction of acid and base-and base-promoted cycloaddition.
Abstract: I Introduction.- II New Synthetic Developments.- A Annulation Reactions.- 1 Acid-and Base-Promoted Cyclizations.- 2 Metal-Promoted Ring Closures.- 3 Free Radical Processes.- 4 [3 +2] Cycloaddition Methodology.- 5 Weiss-Cook Condensations.- 6 Intramolecular Diels-Alder Reactions.- 7 Cyclization of Diazo Compounds.- 8 Miscellaneous.- B Ring Expansion, Contraction, and Cleavage Processes.- C Pauson-Khand Reaction.- D Photochemical Approaches.- 1 Oxa-di-?-methane Entry.- 2 Meta Olefin Addition to Arenes.- E Rearrangement Routes to Polyquinanes.- 1 Thermochemical Pathways.- 2 Cleavage of Cage Molecules.- 3 Carbocation-Based Approaches.- 4 Photochemical Processes.- 5 Base-Promoted Isomerizations.- 6 Carbenic and Transition Metal-Catalyzed Schemes.- F Trapping of 1,3-Diyls.- G Transannular Cyclizations.- III Functional Group Manipulation Within Polyquinanes.- A Reactions Involving Ketonic Substrates.- B Carbocationic Processes.- C Reactions Involving Olefinic Centers.- D Miscellaneous.- IV Physical Data for, and Theoretical Analysis of, Polyquinanes.- A Crystal Structure Data.- B Photoelectron Spectra.- C Molecular Orbital Calculations.- D Miscellaneous.- V Molecules of Theoretical Interest.- A Pentalene.- B Semibullvalenes.- C Syn/anti-Sesquinorbornenes.- D Triquinacenes.- E Tricyclic [10]Annulenes.- F Fenestranes and Related Molecules.- G (D3)-Trishomocubanes and Congeners.- H Peristylanes.- I Chemistry Surrounding Dodecahedrane.- VI Natural Products Chemistry.- A Isolation and Physical Properties.- B Biosynthesis and Chemical Transformations.- VII Synthesis of Nonpolycyclopentanoid Natural Products by Way of Diquinane Intermediates.- A Allamcin.- B Boonein.- C BrefeldinA.- D Dendrobine.- E Forsythide Aglycone Dimethyl Ester.- F Ikarugamycin.- G Iridodial.- H Isoiridomyrmecin.- I Loganin and Analogues.- J Oplopanone.- K Plumericin.- L Trichodiene.- M Udoteatrial.- N Xylomollin.- VIII Synthesis of Diquinane Natural Products.- A Cedranoids.- B The Pentalenolactone Group.- C Quadrone and Terrecyclic Acid.- D Ptychanolide.- E Albene.- F Carbaprostacyclins.- G Ryanodine and the Ryanoid Insecticides.- IX Synthesis of Triquinane Natural Products.- A Linear Triquinanes.- 1 Hirsutene.- 2 The Capnellene Group.- 3 Coriolin.- 4 Hirsutic Acid.- B Angular Triquinanes.- 1 Isocomene Sesquiterpenes.- 2 Silphinene.- 3 Pentalenene and Pentalenic Acid.- 4 Senoxydene.- 5 Silphiperfolene and Congeners.- 6 Retigeranic Acid.- C Propellane Structures.- 1 Modhephene.- X References.

10 citations


Book ChapterDOI
01 Jan 1987
TL;DR: Di- and triquinanes have increasingly found service as building blocks for construction of natural products lacking formal polycyclopentanoid frameworks as mentioned in this paper, and the most recent applications of successful strategems of this type are surveyed.
Abstract: Di- and triquinanes have increasingly found service as building blocks for construction of natural products lacking formal polycyclopentanoid frameworks [374]. In this segment of the review, the most recent applications of successful strategems of this type are surveyed.

4 citations


Book ChapterDOI
01 Jan 1987
TL;DR: In this paper, a range of different strategies to provide access to the tricyclopentanoid ring system of hirsutene have been described, including annulation procedures for their construction.
Abstract: Hirsutene (1124) is the simplest member of a group of fungal metabolites possessing the linearly fused cis,anti,cis-tricyclo[6.3.0.02,6]undecane carbon skeleton [503]. As a result of the antibiotic and antitumor properties shown by some of these triquinanes, synthetic chemists have strived to devise new annulation procedures for their construction. Several new syntheses of hirsutene itself have recently been reported where a wide range of different strategies to provide access to the tricyclopentanoid ring system are described.

2 citations


Book ChapterDOI
01 Jan 1987
TL;DR: In recent years, the tricyclic cedranoid sesquiterpenes have continued to be the subject of numerous synthetic studies as mentioned in this paper, which has resulted in a wide variety of synthetic approaches.
Abstract: In recent years, the tricyclic cedranoid sesquiterpenes have continued to be the subject of numerous synthetic studies. The novel carbocyclic framework of this group of natural products has resulted in a wide variety of synthetic approaches.

1 citations


Book ChapterDOI
01 Jan 1987
TL;DR: Lee and Richardson as discussed by the authors showed that cyclopentannulate silyl enol ethers in a one-pot two-step process can yield a doubly functionalized product without annihilation of the allylsilane moiety.
Abstract: Lee and Richardson have disclosed that it is entirely feasible to cyclopentannulate silyl enol ethers in a one-pot two-step process. For example, condensation of 1 with the readily available stannane 2 in the presence of trimethylsilyl triflate leads to an adduct that cyclizes to 3 on subsequent exposure to titanium tetrachloride [5]. This new strategy is notable in that a doubly functionalized product results. 1,2-Bis(trimethylsilyloxy)cyclopentene (4) condenses with chloride 5 in the presence of anhydrous zinc chloride to give a 1:1 mixture of 6 and 7 [6]. The first relevant point is that alkylation proceeds without annihilation of the allylsilane moiety. Consequently, this functionality is available for subsequent ring closure as illustrated by the independent conversion of 6 and 7 to 8 and 9, respectively, when treated with ethylaluminum dichloride.

1 citations