A novel enantioselective synthesis of the key intermediate of (−)-huperzine a employing asymmetric palladium-catalyzed bicycloannulation

Kaneko, Satoru; Yoshino, Teruo; Katoh, Tadashi; Terashima, Shiro

doi:10.1016/s0957-4166(97)00048-7

Cited by 50 publications

(25 citation statements)

References 16 publications

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“…The Pdcatalyzed bicycloannulation strategy was adopted independently by Terashima and Bai to develop asymmetric routes which provided the olefin 14 in >90% ee. [29][30] Both groups employed ferrocene based chiral phosphine ligands for inducing asymmetry in this common key step. A chiral auxiliary based version of Kozikowski´s Pd-catalyzed bicycloannulation to huperzine was demonstrated by Langlois et al (Scheme 3).…”

Section: Huperzine Amentioning

confidence: 99%

Synthetic approaches towards huperzine A and B

Sohel¹,

Opatz²

2013

Arkivoc

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Section: Huperzine Amentioning

confidence: 99%

Synthetic approaches towards huperzine A and B

Sohel¹,

Opatz²

2013

Arkivoc

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“…By employing the chiral ferrocene ligand 26 (40 mol%), Kaneko et al obtained the tricyclic product 25 in 92% yield and 64% ee. 76 The ee could be improved to >99% by recrystallization of the endocyclic olefin 27; however, the low yield after recrystallization (37%) coupled with the high loading of 26 diminished the efficiency of this approach. In 2001, He et al reported that the annulation of product 25 could be obtained in 82% yield and 90.3% ee using the ferrocene ligand 28 (11 mol%).…”

Section: Synthetic Studiesmentioning

confidence: 99%

The pharmacology and therapeutic potential of (-)-huperzine A

Tun¹,

Herzon²

2012

JEP

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(−)-Huperzine A (1) is an alkaloid isolated from a Chinese club moss. Due to its potent neuroprotective activities, it has been investigated as a candidate for the treatment of neurodegenerative diseases, including Alzheimer’s disease. In this review, we will discuss the pharmacology and therapeutic potential of (−)-huperzine A (1). Synthetic studies of (−)-huperzine A (1) aimed at enabling its development as a pharmaceutical will be described.

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“…Enantiomeric enrichment was performed by recrystallization of optically crude product from hexane to give optically pure (+)-23 and (-)-23 respectively. Following the reaction steps reported for the preparation of (±)-HupA, the natural (-)-HupA and unnatural (+)-HupA were finally furnished [51,59].…”

Section: Using Chiral Catalyst Via Diastereomeric Separationmentioning

confidence: 99%

Huperzine A, A Potential Therapeutic Agent for Treatment of Alzheimer's Disease

Bai¹,

Tang²,

He³

2000

Current Medicinal Chemistry

200

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HupA is a potent, reversible and selective inhibitor of AChE with a rapid absorption and penetration into the brain in animal tests. It exhibits memory-enhancing activities in animal and clinical trials. Compared to tacrine and donepezil, HupA possesses a longer duration of action and higher therapeutic index, and the peripheral cholinergic side effects are minimal at therapeutic doses. This review article deals with a comprehensive survey of the progress in chemical and pharmacological studies of HupA including the isolation and structure elucidation, pharmacological actions, total synthesis, SAR studies and the future development of HupA. Recently, it has been reported that HupA could reduce neuronal cell death caused by glutamate. The dual bio-activities of HupA would further enhance its value and potentiality as the therapeutic agent for Alzheimer s disease.

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A novel enantioselective synthesis of the key intermediate of (−)-huperzine a employing asymmetric palladium-catalyzed bicycloannulation

Cited by 50 publications

References 16 publications

Synthetic approaches towards huperzine A and B

Synthetic approaches towards huperzine A and B

The pharmacology and therapeutic potential of (-)-huperzine A

Huperzine A, A Potential Therapeutic Agent for Treatment of Alzheimer's Disease

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