Total Synthesis of (±)-Stemoamide

Jacobi, Peter A.; Lee, Kyung-Ae

doi:10.1021/ja9642727

Cited by 64 publications

(47 citation statements)

References 9 publications

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“…It is a good source of 14 stemona alkaloids (Pilli and de Oliveira 2000 ) . Tuberous roots are used for the treatment of bronchitis, pertussis, and tuberculosis (Jacobi and Lee 1997 ). In Bangladesh, the tribal people of Chittagong Hill Tracts (CHT) use tuberous roots and leaves of this plant for the treatment of intestinal worm, cough, and mental disorders.…”

Section: Stemona Tuberosa Lourmentioning

confidence: 99%

“…It is found in the hilly areas of Northeast India, Bangladesh, Myanmar, Thailand, Vietnam, Laos, Cambodia, and the Philippines (Tsi and Duyfjes 2000 ). A total of 14 alkaloids are found in S. tuberosa which are useful in treating bronchitis, pertussis, and tuberculosis (Jacobi and Lee 1997 ;Pilli and de Oliveira 2000 ). In nature, propagation is done by seeds and rootstocks.…”

Section: Stemona Tuberosa Lourmentioning

confidence: 99%

See 1 more Smart Citation

Biodiversity Conservation with Special Reference to Medicinal Climbers: Present Scenario, Challenges, Strategies, and Policies

Sharma

Arya

2015

Biotechnological Strategies for the Conservation of Medicinal and Ornamental Climbers

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Climbing plants typically contribute 2-15 % of the leaf biomass and about 5 % of the wood biomass to forests. In India, they are widely distributed from Nilgiris to Himalayas to Andaman Nicobar Islands. Phylogenetically, climbers are found in over 125 families of fl owering plants as well as among several fern groups and even in one signifi cant gymnosperm genus, Gnetum . They are largely used by all divisions of the population either directly as folk medications or indirectly in the preparation of recent pharmaceuticals. Climbers also play a vital role in horticulture and agriculture. Thus, people depend on climbers for several purposes like for medications, non-timber forest products, food, etc. Nowadays, plant-based pharmaceutical industries have been increased due to various advantages of plant-based medicine over the synthetic ones. Wild plants are the good source to provide the raw materials for such industries. Unfortunately, a huge number of medicinal climbers have been listed in Red Data Book and are on the verge of extinction due to unsustainable collection of plants, habitat loss, climate change, and industrialization coupled with urbanization. Thus, biodiversity conservation is an utmost concern globally. Various strategies are in use for biodiversity conservation such as in situ strategy, ex situ strategy, reduction of anthropogenic pressures, and rehabilitation of threatened species. Protection and preservation of germplasm within national parks, biosphere reserves, and sanctuaries are the examples of in situ conservation. However, it is not an effective means of conservation. In this regard, biotechnological approach like plant tissue culture technique proved to be fruitful. Plant tissue culture can be applied to the rapid propagation and ex situ conservation of rare, endemic, and endangered medicinal plants as explained by several authorities.

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Section: Stemona Tuberosa Lourmentioning

confidence: 99%

Section: Stemona Tuberosa Lourmentioning

confidence: 99%

Biodiversity Conservation with Special Reference to Medicinal Climbers: Present Scenario, Challenges, Strategies, and Policies

Sharma

Arya

2015

Biotechnological Strategies for the Conservation of Medicinal and Ornamental Climbers

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“…Since the unexpected isomer cis-I dominated in the iminium ion cyclization, 8c it implies that the absolute configuration of C8 should be pre-installed in the S- (8) configuration, which will be subsequently epimerized to the designed R-stereochemistry for C8 in (-)-stemoamide. Therefore, S-configured alcohol 6a was used for the enantioselective total synthesis of stemoamide.…”

Section: Preparation Of the Chiral Propargylic Alcoholmentioning

confidence: 99%

“…7c The development of concise synthetic access to stemoamide is still of great interest in the synthetic community today. 8,9 The pyrrolo[1,2-a]azapine ring system represents a classic architecture and serves as a potential precursor for other more complex stemona alkaloids. The recent comprehensive investigation by Aubé and coworkers on structure derivatization inspired from stemona alkaloids led to the discovery of potent chemotype sigma ligands.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Synthesis of (–)-Stemoamide

Hong

Wang

et al. 2012

Synthesis

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An enantioselective synthesis of (-)-stemoamide is presented. Noyori's ruthenium complex catalyzed asymmetric transfer hydrogenation of an alkynone delivered the (S)-C8 stereogenic center in 97.7% ee. An iron(III) chloride promoted and bioinspired Niminium ion cyclization afforded a 3:1 ratio of two diastereomers in favor of the cis-isomer. The diastereomeric ratio was enriched to 50:1 by a silver-catalyzed cycloisomerization. The subsequent dynamic ruthenium-catalyzed CO-insertion reaction secured an enantioselective total synthesis of (-)-stemoamide in 18% overall yield with high optical purity.

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“…[5][6][7] More recently, these azabicyclic cores are key pharmacophores of highthroughput screening (HTS) hits from our MLPCN probe discovery efforts, [8] requiring robust methodology to rapidly access the parent azabicyclic ring systems as well as flexibility to incorporate structural diversity for analogue synthesis. [9] Many synthetic strategies have been developed for the construction of azabicyclic ring systems, [10] such as 1 and 2, including Staudinger-aza-Wittig approaches, [11] 7-exo-tet-A C H T U N G T R E N N U N G cyclizations, [12] [4 + 2] and [2 + 2 + 2] cycloadditions, [13] ringclosing metathesis (RCM) strategies, [14] nitrone rearrangements [15] and intramolecular Schmidt rearrangements. [16] General approaches for the synthesis of the pyrroloA C H T U N G T R E N N U N G [1,2a]azocine 3 system are rare and most lack stereocontrol.…”

mentioning

confidence: 99%

A Versatile Enantioselective Synthesis of Azabicyclic Ring Systems: A Concise Total Synthesis of (+)‐Grandisine D and Unnatural Analogues

Fadeyi

Senter

Hahn

et al. 2012

Chemistry A European J

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Closing in on azacines: We have developed a new six step approach for the rapid and enantioselective synthesis of indolizidine, pyrrolo[1,2‐a]azepine, and pyrrolo[1,2‐a]azocine azabicyclic systems and their respective lactam congeners, which are found in a host of natural products as well as pharmaceutical preparations. This protocol enables a concise enantioselective total synthesis of (+)‐grandisine D in 16.4 % overall yield from commercial materials (see scheme).

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Total Synthesis of (±)-Stemoamide

Cited by 64 publications

References 9 publications

Biodiversity Conservation with Special Reference to Medicinal Climbers: Present Scenario, Challenges, Strategies, and Policies

Biodiversity Conservation with Special Reference to Medicinal Climbers: Present Scenario, Challenges, Strategies, and Policies

Enantioselective Synthesis of (–)-Stemoamide

A Versatile Enantioselective Synthesis of Azabicyclic Ring Systems: A Concise Total Synthesis of (+)‐Grandisine D and Unnatural Analogues

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