Literature DB >> 19788328

A short enantioselective total synthesis of the fundamental pentacyclic triterpene lupeol.

Karavadhi Surendra1, E J Corey.   

Abstract

The first enantioselective synthesis of lupeol has been developed by applying two carefully crafted cation-pi cyclization stages to generate the pentacyclic structure with complete stereocontrol. The synthesis (Scheme 1) is noteworthy because of its brevity and also because it solves a longstanding problem in the field of natural product synthesis.

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Year:  2009        PMID: 19788328     DOI: 10.1021/ja906335u

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


  8 in total

1.  Synthetic access to bent polycycles by cation-pi cyclization.

Authors:  Ryan A Shenvi; E J Corey
Journal:  Org Lett       Date:  2010-08-06       Impact factor: 6.005

2.  Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.

Authors:  Zachary Powers; Adam Scharf; Andrea Cheng; Feng Yang; Martin Himmelbauer; Takaaki Mitsuhashi; Lena Barra; Yoshimasa Taniguchi; Takashi Kikuchi; Makoto Fujita; Ikuro Abe; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-25       Impact factor: 15.336

3.  Terpenoid-Alkaloids: Their Biosynthetic Twist of Fate and Total Synthesis.

Authors:  Emily C Cherney; Phil S Baran
Journal:  Isr J Chem       Date:  2011-04-01       Impact factor: 3.333

4.  Synthesis, In Vitro and In Silico Analysis of New Oleanolic Acid and Lupeol Derivatives against Leukemia Cell Lines: Involvement of the NF-κB Pathway.

Authors:  Gianfranco Fontana; Natale Badalamenti; Maurizio Bruno; Davide Castiglione; Monica Notarbartolo; Paola Poma; Alberto Spinella; Marco Tutone; Manuela Labbozzetta
Journal:  Int J Mol Sci       Date:  2022-06-13       Impact factor: 6.208

Review 5.  Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades.

Authors:  Cheng-Shi Jiang; Lin-fu Liang; Yue-wei Guo
Journal:  Acta Pharmacol Sin       Date:  2012-09-03       Impact factor: 6.150

Review 6.  An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study.

Authors:  Alexander W Schuppe; Yannan Liu; Timothy R Newhouse
Journal:  Nat Prod Rep       Date:  2020-09-15       Impact factor: 13.423

7.  An Improved Scalable Synthesis of α- and β-Amyrin.

Authors:  Immo Serbian; René Csuk
Journal:  Molecules       Date:  2018-06-27       Impact factor: 4.411

Review 8.  Chemical Strategies towards the Synthesis of Betulinic Acid and Its More Potent Antiprotozoal Analogues.

Authors:  André Barreto Cunha; Ronan Batista; María Ángeles Castro; Jorge Mauricio David
Journal:  Molecules       Date:  2021-02-18       Impact factor: 4.411

  8 in total

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