19906-72-0Relevant academic research and scientific papers
Conversion of optically active hydrindanone to (+)-bakkenolide-A
Kusakabe, Taichi,Kato, Keisuke,Motodate, Satoshi,Takaishi, Satoshi,Akita, Hiroyuki
, p. 1436 - 1437 (2008)
A total synthesis of (+)-bakkenolide-A was carried out via the key intermediate 4, which was prepared based on an asymmetric cyclization- carbonylation reaction established in our laboratory. Diastereoselective construction of the spirolactone moiety was achieved using Mitsuhashi's protocol as a key step.
A general approach toward bakkanes: Short synthesis of (±)- bakkenolide-A (Fukinanolide)
Reddy, D. Srinivasa
, p. 3345 - 3347 (2004)
(Chemical Equation Presented) An efficient, general, and fully stereocontrolled approach to the family of bakkanes is disclosed. This route highlights a highly diastereoselective Diels-Alder/aldol sequence to furnish the common hydrindane precursor for th
A ring contraction strategy toward a diastereoselective total synthesis of (+)-bakkenolide A
Carneiro, Vania M. T.,Ferraz, Helena M. C.,Vieira, Tiago O.,Ishikawa, Eloisa E.,Silva Jr., Luiz F.
experimental part, p. 2877 - 2882 (2010/08/13)
A diastereoselective route to (+)-bakkenolide A is presented from the readily available optically active Wieland-Miescher ketone. This novel synthesis of this sesquiterpene lactone features the following as key stereoselective transformations: (i) the ring contraction reaction of a octalone mediated by thallium(III) nitrate (TTN); (ii) a hydrogenation to create the cis-fused junction; and (iii) the formation of the C7 quaternary center through an enolate intermediate. Furthermore, during this work, the absolute configuration of a trinorsesquiterpene isolated from Senecio Humillimus was assigned.
Core structure of eremophilanes and bakkanes through niobium catalyzed Diels-Alder reaction: Synthesis of (±)-bakkenolide A
Constantino, Mauricio G.,De Oliveira, Kleber T.,Polo, Ellen C.,Da Silva, Gil V. J.,Brocksom, Timothy J.
, p. 9880 - 9883 (2007/10/03)
A suitable intermediate for the synthesis of eremophilanes and bakkanes was prepared by a highly regioselective and stereoselective one-step synthesis through a niobium catalyzed Diels-Alder reaction. As a demonstration of the versatility of this intermed
First comprehensive bakkane approach: Stereoselective and efficient dichloroketene-based total syntheses of (±)- and (-)-9-acetoxyfukinanolide, (±)- and (+)-bakkenolide a, (-)-bakkenolides III, B, C, H, L, V, and X, (±)- and (-)-homogynolide A, (±)-homogynolide B, and (±)-palmosalide C
Brocksom, Timothy J.,Coelho, Fernando,Depres, Jean-Pierre,Greene, Andrew E.,Freire de Lima, Marco E.,Hamelin, Olivier,Hartmann, Benoit,Kanazawa, Alice M.,Wang, Yanyun
, p. 15313 - 15325 (2007/10/03)
Cycloaddition of dichloroketene with dimethylcyclohexenes has been used as the key reaction in an efficient, general approach to the bakkanes. New methods and methodologies that have been developed in this work include spiro β-methylene-γ-butyrolactonizations, a vicinal dicarboxylation, an angelic ester preparation, a transesterification, an epoxy ketone double reduction, and a retro aldol-aldol approach to low-energy aldol isomers.
Synthesis of (±)-bakkenolide-A and its C-7, C-10, and C-7,10 epimers by means of an intramolecular Diels-Alder reaction
Back,Nava-Salgado,Payne
, p. 4361 - 4368 (2007/10/03)
(±)-Bakkenolide-A (1) was prepared in five steps from ethyl 4-benzyloxyacetoacetate by sequential alkylations with tiglyl bromide and (Z)-5-bromo-1,3-pentadiene, followed by an intramolecular Diels-Alder reaction of (E,Z)-triene 25b as the key step. The hydrindane cycloadduct 28 was subjected to hydrogenation and spontaneous or acid-catalyzed lactonization, followed by a Witttig reaction to introduce the exocyclic methylene group of 1. The known 7-epibakkenolide-A (2) and novel 10-epi- and 7,10-diepibakkenolide-A (3 and 4, respectively) stereoisomers were obtained as minor byproducts. When (E)-5-bromo-1,3-pentadiene was used instead of the Z-isomer, the 10-epi-and 7,10-diepibakkenolides were the major products. In both cases exo cyclization was preferred over endo. An alternative approach was based on a similar intramolecular Diels-Alder cycloaddition, using dimethyl malonaate instead of ethyl 4-benzyloxyacetoacetate as the starting material for the double alkylation preceding the cycloaddition step. The cycloadduct was then converted into the corresponding α-phenylseleno propargyl esters 16 or 22. However, attempted formation of the spiro center by a radical cyclization resulted chiefly in reductive deselenization.
A concise total synthesis of (+/-)-bakkenolide A by means of an intramolecular Diels-Alder reaction.
Back,Payne
, p. 663 - 665 (2008/02/11)
(+/-)-Bakkenolide A was prepared in five steps from ethyl 4-benzyloxyacetoacetate by sequential alkylations with tiglyl bromide nd cis-5-bromo-1,3-pentadiene, followed by an intramolecular Diels-Alder reaction as the key step. The known 7-epibakkenolide A
A Stereoselective Total Synthesis of Bakkenolide-A (Fukinanolide)
Srikrishna, Adusumilli,Jagadeeswar Reddy, T.,Nagaraju, Sankuratri,Sattigeri, Jitendra A.
, p. 7841 - 7844 (2007/10/02)
A highly stereoselective synthesis of bakkenolide-A (fukinanolide, 1a) employing the radical mediated spirannulation methodology is described.
