Literature DB >> 12381175

Synthesis of (-)-morphine.

Douglass F Taber1, Timothy D Neubert, Arnold L Rheingold.   

Abstract

The preparation of the diastereomerically pure beta-tetralone ketal 4 is reported. Intramolecular alkylidene C-H insertion followed by hydrolysis of 4 proceeded to give the enantiomerically pure cyclopentene 15. The key step in this synthesis was the bis-intramolecular cyclization of keto aldehyde 2 to give the tetracyclic intermediate 20. Enone 20 was converted over several steps to (-)-morphine 1.

Entities:  

Mesh：

Substances：

Year:  2002        PMID： 12381175     DOI： 10.1021/ja027882h

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  9 in total

1.  Enantioselective Synthesis of Hydrobenzofuranones Using an Asymmetric Desymmetrizing Intramolecular Stetter Reaction of Cyclohexadienones.

Authors:  Qin Liu; Tomislav Rovis
Journal:  Org Process Res Dev       Date:  2007       Impact factor: 3.317

2.  Asymmetric synthesis of hydrobenzofuranones via desymmetrization of cyclohexadienones using the intramolecular Stetter reaction.

Authors:  Qin Liu; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

3.  Enantioselective synthesis of (+)-majusculone.

Authors:  Douglass F Taber; M Inthikhab Sikkander; Pierre H Storck
Journal:  J Org Chem       Date:  2007-04-21       Impact factor: 4.354

Review 4.  Fukuyama reduction, Fukuyama coupling and Fukuyama-Mitsunobu alkylation: recent developments and synthetic applications.

Authors:  Sana Sikandar; Ameer Fawad Zahoor; Shazia Naheed; Bushra Parveen; Kulsoom Ghulam Ali; Rabia Akhtar
Journal:  Mol Divers       Date:  2021-02-11       Impact factor: 2.943

5.  A Cascade Strategy Enables a Total Synthesis of (±)-Morphine.

Authors:  Shuyu Chu; Niels Münster; Tudor Balan; Martin D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-13       Impact factor: 15.336

6.  Programmed serial stereochemical relay and its application in the synthesis of morphinans.

Authors:  Kun Ho Kenny Park; Rui Chen; David Y-K Chen
Journal:  Chem Sci       Date:  2017-08-30       Impact factor: 9.825

7.  Asymmetric synthesis of (-)-naltrexone.

Authors:  Sun Dongbang; Blaine Pedersen; Jonathan A Ellman
Journal:  Chem Sci       Date:  2018-10-23       Impact factor: 9.825

8.  Preparation of chiral 3-oxocycloalkanecarbonitrile and its derivatives by crystallization-induced diastereomer transformation of ketals with chiral 1,2-diphenylethane-1,2-diol.

Authors:  Yohei Yamashita; Daisuke Maki; Shiho Sakurai; Takumi Fuse; Shoji Matsumoto; Motohiro Akazome
Journal:  RSC Adv       Date:  2018-09-21       Impact factor: 3.361

9.  Mechanistic studies on the CAN-mediated intramolecular cyclization of δ-aryl-β-dicarbonyl compounds.

Authors:  Brian M Casey; Dhandapani V Sadasivam; Robert A Flowers Ii
Journal:  Beilstein J Org Chem       Date:  2013-07-23       Impact factor: 2.883
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.