With Tag: Alkaloids

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Preparation and Synthetic Applications of 2-Halotryptamines:  Synthesis of Elacomine and Isoelacomine

Fumiko Y. Miyake, Kenichi Yakushijin, David A. Horne
Org. Lett. | 2004 | 10.1021/ol030138x

The preparation of 2-halotryptamines from tryptamine is described. New stereoselective intramolecular iminium ion spirocyclization methodology for the construction of spiro[pyrrolidine-3,3‘-oxindoles] is outlined in synthetic studies of elacomine (1) and...


Evolution of the Vinylogous Mannich Reaction as a Key Construction for Alkaloid Synthesis

Stephen F. Martin
Acc. Chem. Res. | 2002 | 10.1021/ar950230w

The vinylogous Mannich reaction is rapidly emerging as an important process for the construction of derivatives of δ-aminocarbonyl compounds. Because the iminium and dienol components employed in this addition may be either acyclic or cyclic, a wide variety...


Asymmetric Synthesis of Functionalized trans-2,6-Disubstituted Piperidines with N-Sulfinyl δ-Amino β-Ketoesters. Synthesis of (−)-Lasubine I

Ashwin Rao, Franklin A. Davis, Patrick J. Carroll
Org. Lett. | 2003 | 10.1021/ol035390j

The hydroxy-directed reduction of 1,2-dehydropiperidines with the “ate” complex of DIBAL-H and n-BuLi affords functionalized trans-2,6-disubstituted piperidines. This methodology was employed in the asymmetric synthesis of the quinolizidine alkaloid...


A Direct and Efficient Total Synthesis of the Tubulin-Binding Agents Ceratamine A and B; Use of IBX for a Remarkable Heterocycle Dehydrogenation

Robert S. Coleman, Erica L. Campbell, Daniel J. Carper
Org. Lett. | 2009 | 10.1021/ol900709n

The total synthesis of the tubulin-binding agents ceratamine A and B is reported, along with des-methyl analogs, via a synthetic route that is high-yielding and operationally efficient. The synthetic route involved a Beckmann rearrangement to form an azepine...


Synthesis of the Tetracyclic Core of Tetrapetalone A Enabled by a Pyrrole Reductive Alkyation

Richmond Sarpong, Andrew P. Marcus
Org. Lett. | 2010 | 10.1021/ol1018536

The tetracyclic framework of the tetrapetalone A aglycon has been secured through synthesis. A reductive pyrrole alkylation enables the formation of a key tetrasubstituted carbon stereocenter, and the tetramic acid portion of the molecule can be accessed...


Interrupted Fischer Indolization Approach toward the Communesin Alkaloids and Perophoramidine

Neil K. Garg, Grace Chiou, Alex W. Schammel
Org. Lett. | 2012 | 10.1021/ol302023q

A concise approach toward the total synthesis of the communesin alkaloids and perophoramidine is reported. The strategy relies on the use of the interrupted Fischer indolization to build the tetracyclic indoline core of the natural products. Studies to probe...


Flexible Approach to Stemona Alkaloids: Total Syntheses of (−)-Stemospironine and Three New Diastereoisomeric Analogs

Francisco Sánchez-Izquierdo, Félix Busqué, Josep Font, Nuria Bardají, Marta Figueredo, Ramón Alibés
Org. Lett. | 2012 | 10.1021/ol302185j

Total syntheses of (−)-stemospironine and three new diastereoisomeric analogs have been completed through a flexible strategy devised for Stemona alkaloids. The azabicycle 7 is the pivotal intermediate, from which the sequence splits according to each...


A Concise Asymmetric Synthesis of the ADE Fragment of Nakadomarin A

Kateri A. Ahrendt, Robert M. Williams
Org. Lett. | 2005 | 10.1021/ol050201d



Biomimetic Synthesis and Biological Evaluation of Aplidiopsamine A

Joseph D. Panarese, Craig W. Lindsley
Org. Lett. | 2012 | 10.1021/ol3024665

The first total synthesis of Aplidiopsamine A, a rare 3H-pyrrolo[2,3-c]quinoline alkaloid from the Aplidiopsis confluata, has been achieved following the proposed biosynthesis. This biomimetic synthesis requires only five steps and proceeds in 20.8% overall...


Synthesis of (+)-Lycoricidine by the Application of Oxidative and Regioselective Ring-Opening of Aziridines

J. S. Yadav, G. Satheesh, Changalvala V. S. R. Murthy
Org. Lett. | 2010 | 10.1021/ol100755v

A highly stereoselective total synthesis of (+)-lycoricidine has been described. The salient features of this synthesis are the one-pot elimination followed by allylation reaction, ring-closing metathesis, stereoselective aziridine formation, Dess−Martin...


Total Synthesis of (−)-Herbindoles A, B, and C via Transition-Metal-Catalyzed Intramolecular [2 + 2 + 2] Cyclization between Ynamide and Diynes

Nozomi Saito, Taisuke Ichimaru, Yoshihiro Sato
Org. Lett. | 2012 | 10.1021/ol300571b

The total syntheses of (−)-herbindoles A, B, and C as naturally occurring forms were accomplished for the first time through transition-metal-catalyzed intramolecular [2 + 2 + 2] cyclization between ynamide and diynes. This strategy provided a highly...


One-Pot Organocatalytic Enantioselective Domino Double-Michael Reaction and Pictet-Spengler–Lactamization Reaction. A Facile Entry to the “Inside Yohimbane” System with Five Contiguous Stereogenic Centers

Wei-Kai Liao, Nitin S. Dange, Bor-Cherng Hong, Ju-Hsiou Liao
Org. Lett. | 2013 | 10.1021/ol3032329

An expedited method was developed for the enantioselective synthesis of dodecahydrobenz[a]indolo[3,2-h]quinolizine containing five contiguous stereogenic centers with high enantioselectivities (>99% ee). The methodology comprises a domino organocatalytic...


Total Synthesis of the Natural Product (±)-Dibromophakellin and Analogues

Jetze J. Tepe, Nicole M. Hewlett
Org. Lett. | 2012 | 10.1021/ol300329h



Total Syntheses of (−)- and (+)-Goniomitine

Ikumi Tamai, Chisato Mukai, Chihiro Yanagihara, Fuyuhiko Inagaki, Masaya Mizutani, Takeo Nakanishi
Org. Lett. | 2011 | 10.1021/ol200320z

The Stille coupling reaction of 3-(benzyloxymethyl)-1-(tert-butyldiphenylsiloxy)ethyl-1-(tributylstannyl)allene with N-(tert-butoxycarbonyl)-2-iodoaniline directly produced the corresponding 2-vinylindole derivative, which was independently transformed into...


A Concise Synthesis of Butylcycloheptylprodigiosin

Jonathan T. Reeves
Org. Lett. | 2007 | 10.1021/ol070341i

A short and efficient total synthesis of the tripyrrole alkaloid butylcycloheptylprodigiosin is described. Key to the brevity of the approach is a two-step synthesis of macrocyclic formylpyrrole 4 from cyclononenone 6.


A Concise Total Synthesis of (−)-Cylindricine C through a Stereoselective Intramolecular Aza-[3 + 3] Annulation Strategy

Jacob J. Swidorski, Richard P. Hsung, Jiashi Wang
Org. Lett. | 2006 | 10.1021/ol053059p

An enantioselective total synthesis of (−)-cylindricine C is described, featuring a diastereoselective intramolecular aza-[3 + 3] annulation strategy and an interesting halohydrin formation of the C4−5 olefin for construction of C4-ketone. This work...


Synthesis of the Tricyclic Core of Colchicine via a Dienyne Tandem Ring-Closing Metathesis Reaction

Issam Hanna, François-Didier Boyer
Org. Lett. | 2007 | 10.1021/ol070708j

The synthesis of the tricyclic framework of colchicine has been achieved using a tandem ring-closing metathesis reaction of dienynes as the key step. In this process, both seven-membered rings B and C were formed in one step. Oxidation of tertiary allylic...


Synthesis of the Western Half of the Lolicines and Lolitrems

Dylan B. England, Jakob Magolan, Michael A. Kerr
Org. Lett. | 2006 | 10.1021/ol060338j

The synthesis of the highly substituted indole portion of the complex tremorgenic natural products lolicine A and B is presented. The Diels−Alder reaction of a quinone monoimine enables the synthesis of an appropriately substituted indole. The key step in...


Chemoenzymatic Approaches to Lycorine-Type Amaryllidaceae Alkaloids:  Total Syntheses of ent-Lycoricidine, 3-epi-ent-Lycoricidine, and 4-Deoxy-3-epi-ent-lycoricidine

Martin G. Banwell, Maria Matveenko, Okanya J. Kokas, Anthony C. Willis
Org. Lett. | 2007 | 10.1021/ol701552r

The readily available and enzymatically derived cis-1,2-dihydrocatechol 4 has been elaborated, over 11 steps including an Overman rearrangement, into the non-natural enantiomer, (−)-1, of the alkaloid lycoricidine [(+)-1]. Related chemistries have provided...


Total Synthesis of (+)-Lepadin F

Richard P. Hsung, Gang Li, Brian W. Slafer, Irina K. Sagamanova
Org. Lett. | 2008 | 10.1021/ol802068q


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