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Akuammicine

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Rodrigo B Andrade – One of the best experts on this subject based on the ideXlab platform.

G. Hugel – One of the best experts on this subject based on the ideXlab platform.

Gopal Sirasani – One of the best experts on this subject based on the ideXlab platform.

  • Total Synthesis of Strychnos Alkaloids Akuammicine, Strychnine, and Leuconicines A and B
    Strategies and Tactics in Organic Synthesis, 2013
    Co-Authors: Gopal Sirasani, Rodrigo B Andrade
    Abstract:

    Abstract Described herein is an account of my laboratory’s entry into the magnificent field of complex alkaloid total synthesis, spanning the development of novel methods for quickly assembling polycyclic frameworks through the total synthesis of various members of the Strychnos alkaloids. A discussion of the prior art related to our approach to these alkaloids in addition to strategic decisions and reasoning made en route to targets Akuammicine ( 1 ), strychnine ( 2 ), and leuconicines A ( 3 ) and B ( 4 ) is carefully detailed. Finally, we present the retrosynthetic analyses of the aforementioned targets and respective total syntheses thereof (including asymmetric variants).

  • Concise Total Synthesis of (.+-.)-Strychnine and (.+-.)-Akuammicine.
    ChemInform, 2010
    Co-Authors: Gopal Sirasani, Tapas Paul, Scott Kassel, William Jr. Dougherty, Rodrigo B Andrade
    Abstract:

    The formation of the title compounds is achieved via previously reported sequential one-pot spirocyclization/intramolecular aza-Baylis—Hillman procedure.

  • concise total synthesis of strychnine and Akuammicine
    ChemInform, 2010
    Co-Authors: Gopal Sirasani, Tapas Paul, Scott Kassel, William Jr. Dougherty, Rodrigo B Andrade
    Abstract:

    The formation of the title compounds is achieved via previously reported sequential one-pot spirocyclization/intramolecular aza-Baylis—Hillman procedure.

Yong Tang – One of the best experts on this subject based on the ideXlab platform.

Jean Lévy – One of the best experts on this subject based on the ideXlab platform.

  • Flow Thermolysis Rearrangements in the Indole Alkaloid Series: Strictamine and Akuammicine Derivatives. The Absolute Configurations of Ngouniensine and epi-Ngouniensine.
    The Journal of organic chemistry, 1997
    Co-Authors: G. Hugel, Daniel Royer, Louisette Le Men-olivier, Bernard Richard, Marie-josé Jacquier, Jean Lévy
    Abstract:

    Flow thermolysis of strictamine (1) generated two of the predictable rearrangement products, resulting from [1,5]-sigmatropic shifts:  Akuammicine (2) and indolenine 9. Besides formation of these two compounds, a quite different pathway gave rise to a novel rearrangement leading to indole 6, with the framework of the natural alkaloid ngouniensine (19). Rearrangement to the ngouniensine skeleton became the major pathway when the Akuammicine derivatives 10, 12, and 17 were submitted to thermolysis, generating compounds 11, 13 + 15, and 18, respectively. These results allowed us to assign the absolute configuration of (−)-ngouniensine (19) (3R,20R) and that of (−)-epingouniensine ((−)-21) (3R,20S).