Heterocycle formation through aza-annulation: A stereochemically controlled route to (±)-lupinine

DOI: 10.1016/S0040-4039(00)60550-6

Source and publish data:

Tetrahedron Letters p. 215 - 218 (1993)

Update date:2022-07-30

Topics:

Authors:

Paulvannan

Schwarz Schwarz

Stille Stille

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1016/S0040-4039(00)60550-6

The aza-annulation of an acyclic β-enaminoester with acryloyl chloride was found to be a very efficient method for nitrogen heterocycle formation. Stereospecific hydrogenation of the unsaturated dihydropyridone generated from aza-annulation gave a single disubstituted lactam product. The cis stereochemical relationship of the substituents was confirmed by transformation of the lactam to (±)-lupinine.

Full text of DOI:10.1016/S0040-4039(00)60550-6

Products guided by the article

Product name:(Z)-3-Benzylamino-7-benzyloxy-hept-2-enoic acid ethyl ester

Cas No:146450-46-6

R&D Labs maybe for 146450-46-6

SOGA ENTERPRISES ASIA GROUP

Contact:+86-633-8332928

Address:No.1,Huanghai Yilu.Rizhao,Shandong
Molobelamltrading

Contact:27-792-602929

Address:SIDNEY MUFAMADI STREET 009949 X44 0700 POLOKWANE,LIMPOPO
Dongtai Xinyuan Chemical Co., Ltd.

Contact:+86-21-56733000

Address:404F, 99Nong No.117 Zhongtan Rd. Shanghai
Josun International Limited

website:http://www.josunpharma.com

Contact:+86-311-80715268 80766839

Address:No.39, Zhaiying Street, Shijaizhuang,Hebei,China
Shaanxi Lighte Optoelectronics Material Co., Ltd.

Contact:+86-29-88320728-622/619/620

Address:No.55 INDUSTRY ROAD 2,XI'AN NATIONAL CIVIL AEROSPACE INDUSTRIAL PARK.XI'AN China 710065.

Relevant to this article

General strategy for the stereocontrolled synthesis of Strychnos alkaloids: A concise synthesis of (±)-dehydrotubifoline

Doi:10.1021/ja00060a083
(1993)
6-Alkylthio-1,3-thiazinium-salze aus Acylketen-S,S-acetalen und Thioamiden

Doi:10.1055/s-1982-29748
(1982)
Syntheses, crystal structures and properties of five divalent transition metal coordination compounds based on a semirigid tetracarboxylic acid ligand

Doi:10.1016/j.ica.2013.08.022
(2013)
Combined Photoredox and Lewis Acid Catalyzed α-Hydroxyalkylation of Cyclic Ethers with Aromatic Ketones

Doi:10.1021/acs.joc.6b01085
(2016)
A First Example of Cobalt-Catalyzed Remote C H Functionalization of 8-Aminoquinolines Operating through a Single Electron Transfer Mechanism

Doi:10.1002/adsc.201600161
(2016)
NMR studies of proton transfer in 1:1 Tris(trimethoxyphenyl)-phosphine oxide-phenol complexes

Doi:10.1039/a802219d
(1998)

Article Doi