A Domino Diels-Alder Approach toward the Tetracyclic Nicandrenone Framework.

The tetracarbocyclic framework of the nicandrenone natural products is formed in one step from a linear precursor via a domino intramolecular Diels-Alder/intramolecular furan Diels-Alder/aromatization sequence. The approach represents a new 0 → ABCD strategy for the preparation of aromatic steroids.

[1]  M. Sherburn,et al.  The Diels–Alder Reaction in Steroid Synthesis , 2014, Synthesis.

[2]  C. M. Beaudry,et al.  Synthesis of bis(indole) alkaloids from Arundo donax: the ynindole Diels-Alder reaction, conformational chirality, and absolute stereochemistry. , 2014, Angewandte Chemie.

[3]  Olaia Nieto-García,et al.  IMDAF/aromatization path of halogenated furylacrylamides and furylpropiolamides to dihydroisoquinolin-1(2H)-ones. , 2013, The Journal of organic chemistry.

[4]  P. Wipf,et al.  5-Hydroxyindoles by intramolecular alkynol-furan diels-alder cycloaddition. , 2013, The Journal of organic chemistry.

[5]  Jianji Wang,et al.  Catalyst-free synthesis of diversely substituted 6H-benzo[c]chromenes and 6H-benzo[c]chromen-6-ones in aqueous media under MWI , 2012 .

[6]  A. K. Sarkar,et al.  Intramolecular gold(III) catalysed Diels–Alder reaction of 1-(2-furyl)-hex-1-en-5-yn-3-ol derivatives: a short and generalised route for the synthesis of hydroxyphenanthrene derivatives , 2012 .

[7]  Lu Wang,et al.  Grignard reagent acceleration of the intramolecular Diels-Alder reaction of furans with unactivated alkynes: towards structurally complex oxabicyclic alkenes. , 2011, Chemistry.

[8]  J. Quan,et al.  Formal synthesis of cortistatins. , 2011, The Journal of organic chemistry.

[9]  A. McCluskey,et al.  An Ugi-intramolecular Diels–Alder route to highly substituted tetrahydroepoxyisoindole carboxamides , 2011 .

[10]  J. Quan,et al.  Construction of all-carbon quaternary center by R2AlCl-mediated ring-opening reaction of oxacycles. , 2010, Organic letters.

[11]  Zhen Yang,et al.  A model study for the concise construction of the oxapentacyclic core of cortistatins through intramolecular Diels-Alder and oxidative dearomatization-cyclization reactions. , 2009, Chemical communications.

[12]  S. Bräse,et al.  Highlights in steroid chemistry: total synthesis versus semisynthesis. , 2008, Angewandte Chemie.

[13]  K. Muller,et al.  Regiospecific Synthesis of the C and D Rings of Viridin , 2008 .

[14]  R. Munakata,et al.  Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions. , 2005, Chemical reviews.

[15]  Yundong Wu,et al.  Exploring an expedient IMDA reaction approach to construct the guanacastepene core. , 2005, Organic letters.

[16]  R. Williamson,et al.  The domino intramolecular Diels?Alder approach to 16-oxasteroidsElectronic supplementary information (ESI) available: experimental procedures, product characterisation data and 1H NMR spectra for 8, 9, 11 and 12; ORTEP diagrams for 9 and 11. See http://www.rsc.org/suppdata/cc/b3/b303362g/ , 2003 .

[17]  M. Milanesio,et al.  An Intramolecular Furan−Diene Diels−Alder Approach to 11-Oxo 10α-Steroids , 2002 .

[18]  A. Stephen K. Hashmi,et al.  Highly Selective Gold-Catalyzed Arene Synthesis , 2000 .

[19]  E. Corey,et al.  Enantioselective Total Synthesis of Nicandrenones , 2000 .

[20]  A. Padwa,et al.  Construction of bicyclic tetrahydroisoquinolinones by combination of an IMDAF-ring cleavage reaction of N-allyl-2-furan-2-yl-acetamides , 2000 .

[21]  P. Vogel,et al.  Derivatives of 7-oxabicyclo[2.2.1]heptane in nature and as useful synthetic intermediates , 1999 .

[22]  A. Padwa,et al.  A Cycloaddition Approach toward the Synthesis of Substituted Indolines and Tetrahydroquinolines. , 1999, The Journal of organic chemistry.

[23]  C. Kappe,et al.  Synthetic applications of furan Diels-Alder chemistry , 1997 .

[24]  J. Winkler.  Tandem Diels−Alder Cycloadditions in Organic Synthesis , 1996 .

[25]  W. Roush,et al.  Studies of an intramolecular Diels-Alder approach to the nargenicins: involvement of boatlike transition states in the cyclizations of substituted 1,7,9-decatrien-3-ones , 1989 .

[26]  K. Kanematsu,et al.  New generation and intramolecular Diels-Alder reaction of isobenzofurans: an efficient furan ring-transfer reaction and a synthetic entry into the polycyclic ring systems , 1987 .

[27]  S. Lecker,et al.  Cobalt-catalyzed one-step assembly of B-ring aromatic steroids from acyclic precursors , 1986 .

[28]  Jeffery T. Davis,et al.  Horner-wadsworth-emmons reaction: Use of lithium chloride and an amine for base-sensitive compounds , 1984 .

[29]  A. G. Fallis.  The intramolecular Diels–Alder reaction: recent advances and synthetic applications , 1984 .

[30]  B. Trost,et al.  Palladium-catalyzed 1,3-oxygen-to-carbon alkyl shifts. A cyclopentanone synthesis , 1981 .

[31]  R. Bates,et al.  Structure of Nic-2, a major steroidal constituent of the insect repellent plant Nicandra physaloides , 1974 .

[32]  R. Bates,et al.  Nicandrenone, an insecticidal plant steroid derivative with ring D aromatic. , 1972, Journal of the American Chemical Society.

[33]  F. Zeelen.  Steroid total synthesis. , 1994, Natural product reports.

[34]  L. Harwood,et al.  Synthetic approaches to phorbols via the intramolecular Diels–Alder reaction of furans: influence of the dienophile upon the stereochemical control , 1990 .

[35]  D. Craig.  Stereochemical aspects of the intramolecular Diels–Alder reaction , 1987 .

[36]  P. D. Clercq,et al.  A novel expeditious entry into gibberellins: the total synthesis of (±)-GA5 , 1986 .

[37]  L. Crombie,et al.  A new class of natural steroids, with ring D aromatic, from Nicandra physaloides(solanaceae). X-Ray analysis of Nic-10, and the structures of Nic-1 (‘nicandrenone’),-12, and -17 , 1976 .

[38]  L. Crombie,et al.  Constitution of four novel methyl steroid relatives (ring-D aromatic) from the insect repellent plant Nicandra physaloides; X-ray analysis of Nic-10 , 1972 .

[39]  L. Crombie,et al.  Terpenoid constituents of the insect repellant plant Nicandra physaloides; X-ray structure of a methyl steroid (Nic-3) acetate , 1972 .

[40]  G. Fraenkel,et al.  Insecticides from Plants, Nicandrenone, A New Compound with Insecticidal Properties, Isolated From Nicandra Physalodes , 1964 .