A New Enantioselective Approach to Total Synthesis of the Securinega Alkaloids: Application to (-)-Norsecurinine and Phyllanthine.
نویسندگان
چکیده
An inexpensive proline derivative and chiral control feature in the total synthesis of securinega alkaloids (-)-norsecurinine (1) and phyllanthine (2). Key steps in the synthesis of 1 include an intramolecular ketonitrile coupling and application of a radical-based generation of N-acylimines. The total synthesis of 2 utilizes a stereoselective imino Diels - Alder construction of the methoxypiperidine ring.
منابع مشابه
Total synthesis of securinega alkaloids (-)-norsecurinine, (-)-niruroidine and (-)-flueggine A.
A consecutive synthetic strategy was developed toward the total synthesis of securinega alkaloids. (-)-Norsecurinine was concisely assembled by addition of a methoxyallene to a ketone for efficient side-chain installation. Ring-closing metathesis was also utilized as a key step. The first total synthesis of (-)-niruroidine was achieved from (-)-norsecurinine in three steps, while the route to (...
متن کاملAn approach to the skeleton of the securinega alkaloids. The total synthesis of (+/-)-securinine.
[structure: see text]. The concise total synthesis of securinine in nine steps from readily available starting materials is described. Key steps of the synthesis include an addition of a silyloxyfuran to an in situ generated iminium ion and a novel ring closing metathesis reaction.
متن کاملUltrasonic Irradiation Assisted Enantioselective Synthesis of Alzheimer’s Disease Drug Rivastigmine Tartrate by Using Nanocatalyst
A highly efficient and convenient procedure for the enantioselective synthesis of (S)-Rivastigmine tartrate, a cholinergic agent for the treatment of mild to moderate dementia of the Alzheimer’s disease, is accomplished by the treatment of versatile, readily accessible N-Ethyl-N-methyl carbamoyl chloride with 3-hydroxyacetophenone under ultrasonic irradiation in presence of nano-K2CO3 were repo...
متن کاملChemoenzymatic Enantioselective Formal Synthesis of (-)-Gephyrotoxin-223
(-)-Gephyrotoxin-223 was formally synthesized from chiral synthon 1 which has been chemoenzymatically synthesized in the presence of Candida Antartica lipase.
متن کامل[Synthesis and its application to the synthesis of biologically active natural products of new and versatile chiral building blocks].
This article describes a design and synthesis of new and versatile chiral building blocks and its application to the biologically active natural product synthesis. The chiral building blocks were prepared using a biocatalysis in an enantiomerically pure state. As an application of the above chiral building blocks to the synthesis of biologically active natural product, we demonstrated the diast...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Angewandte Chemie
دوره 39 1 شماره
صفحات -
تاریخ انتشار 2000