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.
Extremely Short Chiral Synthesis of Bicyclic Alkaloids Having a Nitrogen Atom Ring Juncture
Nagao, Yoshimitsu,Dai, Wei-Min,Ochiai, Masahito,Tsukagoshi, Shigeru,Fujita, Eiichi
, p. 289 - 291 (1988)
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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
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.
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
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.
Rhodium-Catalyzed Domino Hydroformylation/Double-Cyclization Reaction of Arylacetylenecarboxamides: Diastereoselectivity Studies and Application in the Synthesis of 1-Azabicyclo[x.y.0]alkanes
Tsai, Jui-Chi,Lin, Yi-Huei,Chen, Guei-Tang,Gao, Yu-Kai,Tseng, Yu-Che,Kao, Chien-Lun,Chiou, Wen-Hua
, p. 3190 - 3197 (2018/10/25)
A domino method for the rapid syntheses of 1-azabicyclo[x.y.0]alkane scaffolds, such as indolizidines, quinolizidines, decahydropyridoazepines, and their derivatives, has been developed. This strategy involved a rhodium-catalyzed hydroformylation of allyl
