Stereoselective synthesis of the tetracyclic core of manzamine via the vinylogous amide photocycloaddition cascade

DOI: 10.1016/S0040-4020(98)00346-9

Source and publish data:

Tetrahedron p. 7045 - 7056 (1998)

Update date:2022-07-30

Topics:

Authors:

Winkler, Jeffrey D.

Axten, Jeffrey

Hammach, Abdel Hakim

Kwak, Young-Shin

Lengweiler, Urs

Lucero, Melissa J.

Houk Houk

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

Article abstract of DOI:10.1016/S0040-4020(98)00346-9

The stereoselective preparation of the tetracyclic core of the manzamine alkaloids via the intramolecular vinylogous amide photocycloaddition/retro- Mannich fragmentation/Mannich closure cascade is described. The striking effect of unsaturation in the eight-membered ring on the stereoselectivity of the cycloaddition and a computational analysis of these results are presented.

Full text of DOI:10.1016/S0040-4020(98)00346-9

Products guided by the article

Product name:5-{(R)-2-Allyloxycarbonylamino-2-[((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-ethyl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Cas No:211511-70-5

R&D Labs maybe for 211511-70-5

Suzhou Wedo Chemicals Co., Ltd.

Contact:86 512 58100425

Address:Zonger Road, DongSha Industry Park , Zhangjiagang, Jiangsu, China
Shanghai Yudiao Chemistry Technology Co.,Ltd

Contact:0086-18964703211

Address:Building NO.5, NO.218,Rongtian Road,ganxiang town,Jinshan District,shanghai,201518,china
qingdao goldenchem imp and exp co.,ltd.

Contact:532-55579246

Address:no.62 ,haier road laoshan distirct
Jiangsu Zenji Pharmaceuticals LTD

Contact:+86-025-83172562; +1-224-888-1133(USA)

Address:No.5 Xinmofan Road
Chengda Pharmaceuticals Co., Ltd.

Contact:+86-573-84601188

Address:hengshan Road 5# in Jiashan, zhejiang

Relevant to this article

Highly chemoselective hydrogenation with retention of the epoxide function using a heterogeneous Pd/C - Ethylenediamine catalyst and THF

Doi:10.1002/1521-3765(20000616)6:12<2200::AID-CHEM2200>3.0.CO;2-3
(2000)
Reduced N -alkyl substituted bis(imino)pyridine cobalt complexes: Molecular and electronic structures for compounds varying by three oxidation states

Doi:10.1021/ic100717w
(2010)
Doi:10.1021/ja01268a051
(1938)
One-pot synthesis of a natural product inspired pyrrolocoumarine compound collection by means of an intramolecular 1,3-dipolar cycloaddition as key step

Doi:10.1016/j.tetlet.2015.01.021
(2015)
Novel liquid crystal aldoximes and aldoxime ethers: Synthesis, characterization and liquid crystal behavior

Doi:10.1016/j.molliq.2015.04.016
(2016)
A library approach to the discovery of small molecules that recognize RNA: Use of a 1,3-hydroxyamine motif as core

Doi:10.1021/ja980826p
(1998)

Article Doi