111975-29-2Relevant articles and documents
A concise synthesis of tashiromine
McElhinney, Alison D.,Marsden, Stephen P.
, p. 2528 - 2530 (2005)
A concise (six-step) synthesis of the indolizidine alkaloid tashiromine (1) has been achieved. Olefin cross-metathesis was used to prepare a key functionalised allylsilane, which subsequently underwent electrophile-induced ring-closure to establish the bicyclic framework with complete control of stereochemistry. Georg Thieme Verlag Stuttgart.
New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates
Riley, Darren L.,Michael, Joseph P.,De Koning, Charles B.
, p. 2609 - 2613 (2016)
The syntheses of the naturally occurring indolizidine alkaloid (±)-tashiromine and its unnatural epimer (±)-epitashiromine are demonstrated through the use of enaminone chemistry. The impact of various electron-withdrawing substituents at the C-8 position of the indolizidine core on the preparation of the bicyclic system is described.
Electroreductive intramolecular coupling of aliphatic cyclic imides with α,β-unsaturated esters and ketones: Unusual methyl-alkoxy exchange in silyl ketene acetals
Kise, Naoki,Inoue, Yusuke,Sakurai, Toshihiko
, p. 3281 - 3285 (2013)
The electroreductive intramolecular coupling of aliphatic cyclic imides with α,β-unsaturated esters in the presence of chlorotrimethylsilane and subsequent desilylation with TBAF gave five- and six-membered cyclized esters and one-carbon elongated methyl
Epoxides as Precursors to 1-Hydroxymethyl Indolizidine and Pyrrolizidine
Hildebrandt, Sven,Schacht, Jonathan H.,Gans?uer, Andreas
, p. 2943 - 2948 (2017)
Herein we describe the synthesis of 1-hydroxymethyl pyrrolizidine and indolizidine alkaloids from epoxy-tethered pyrrole precursors. Two titanium-based methods are evaluated for the construction of the bicyclic scaffold: the Lewis acid mediated cyclizatio
The influence of chiral auxiliaries and catalysts on the selectivity of intramolecular conjugate additions of pyrrole to N-tethered Michael acceptors
Banwell, Martin G.,Beck, Daniel A.S.,Smith, Jason A.
, p. 157 - 159 (2004)
A series of pyrroles incorporating N-tethered acrylates and related groups has been prepared and examined for their capacity to undergo intramolecular Michael addition reactions to form, in a diastereo- or enantio-selective fashion, the corresponding 8-substituted tetrahydroindolizidine or homologues thereof.
Enantioselective Aza-Sakurai Cyclizations: Dual Role of Thiourea as H-Bond Donor and Lewis Base
Park, Yongho,Schindler, Corinna S.,Jacobsen, Eric N.
, p. 14848 - 14851 (2016)
An enantioselective, catalytic aza-Sakurai cyclization of chlorolactams has been developed as an efficient entry into indolizidine and quinolizidine frameworks. Structure-enantioselectivity relationship studies and mechanistic analysis point to a dual role of the catalyst wherein the thiourea moiety of the catalyst is engaged in both anion binding and Lewis base activation of a substrate.
Short and stereodivergent syntheses of (-)-5-epi-tashiromine and (-)-tashiromine and the formal synthesis of (-)-isoretronecanol and (-)-trachelanthamidine
Gavhane, Kishor B.,Bhorkade, Shashikant B.,Kulkarni, Mukund G.
, p. 746 - 750 (2015)
Abstract A successful application of the Wittig-olefination-Claisen rearrangement protocol gave the allyl vinyl ether 12, which was efficiently converted into (-)-tashiromine alkaloids in a short sequence with high overall yield.
Novel stereocontrolled syntheses of tashiromine and epitashiromine
Kiss, Loránd,Forró, Eniko,Fül?p, Ferenc
, p. 596 - 603 (2015)
A novel stereocontrolled approach has been developed for the syntheses of tashiromine and epitashiromine alkaloids from cyclooctene β-amino acids. The synthetic concept is based on the azetidinone opening of a bicyclic β-lactam, followed by oxidative ring
Activating Imides with Triflic Acid: A General Intramolecular Aldol Condensation Strategy Toward Indolizidine, Quinolizidine, and Valmerin Alkaloids
Quevedo-Acosta, Yovanny,Jurberg, Igor D.,Gamba-Sánchez, Diego
, p. 239 - 243 (2020/01/02)
A simple, inexpensive, step economic, and highly modular synthetic strategy to access izidine alkaloids is described. The key step is a TfOH-promoted intramolecular aldol condensation between enol and cyclic imide moieties. This cyclization strategy can be employed within an aza-Robinson annulation framework and represents a general tool to build fused bicyclic amines. To illustrate the power of this method, we describe the preparation of (±)-coniceine, (±)-quinolizidine, (±)-tashiromine, (±)-epilupinine, and the core of (±)-valmerins.
A Concise Asymmetric Total Synthesis of (+)-Epilupinine
Tsutsumi, Tomohiro,Karanjit, Sangita,Nakayama, Atsushi,Namba, Kosuke
supporting information, p. 2620 - 2624 (2019/04/30)
Asymmetric total synthesis of (+)-epilupinine was achieved in just three steps using only commercially available common reagents. The total synthesis involved alkylations of N-nosylamide, ozone oxidation, and sequential reactions of the removal of the nosyl group, intramolecular dehydrative condensation, intramolecular Mannich reaction catalyzed by l-proline, and a reduction.
