Literature DB >> 22924668

Stereoselective synthesis of acortatarins A and B.

Jacqueline M Wurst1, Alyssa L Verano, Derek S Tan.   

Abstract

Acortatarins A and B have been synthesized via stereoselective spirocyclizations of glycals. Mercury-mediated spirocyclization of a pyrrole monoalcohol side chain leads to acortatarin A. Glycal epoxidation and reductive spirocyclization of a pyrrole dialdehyde side chain leads to acortatarin B. Acid equilibration and crystallographic analysis indicate that acortatarin B is a contrathermodynamic spiroketal with distinct ring conformations compared to acortatarin A.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22924668      PMCID： PMC3466107          DOI： 10.1021/ol3019456

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  19 in total

1.  Diastereoselective synthesis of the C(17)-C(28) fragment (the C-D spiroketal unit) of spongistatin 1 (altohyrtin A) via a kinetically controlled iodo-spiroketalization reaction.

Authors:  Edward B Holson; William R Roush
Journal:  Org Lett       Date:  2002-10-17       Impact factor: 6.005

2.  Chiral phosphoric acid-catalyzed enantioselective and diastereoselective spiroketalizations.

Authors:  Zhankui Sun; Grace A Winschel; Alina Borovika; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2012-05-07       Impact factor: 15.419

3.  Total synthesis and stereochemical revision of acortatarins A and B.

Authors:  Gangarajula Sudhakar; Vilas D Kadam; Shruthi Bayya; Gavinolla Pranitha; Bharatam Jagadeesh
Journal:  Org Lett       Date:  2011-09-28       Impact factor: 6.005

4.  Stereocontrolled synthesis of spiroketals via a remarkable methanol-induced kinetic spirocyclization reaction.

Authors:  Justin S Potuzak; Sirkka B Moilanen; Derek S Tan
Journal:  J Am Chem Soc       Date:  2005-10-12       Impact factor: 15.419

5.  Asymmetric spiroacetalization catalysed by confined Brønsted acids.

Authors:  Ilija Čorić; Benjamin List
Journal:  Nature       Date:  2012-03-14       Impact factor: 49.962

6.  Reveromycin A biosynthesis uses RevG and RevJ for stereospecific spiroacetal formation.

Authors:  Shunji Takahashi; Atsushi Toyoda; Yasuyo Sekiyama; Hiroshi Takagi; Toshihiko Nogawa; Masakazu Uramoto; Ryuichiro Suzuki; Hiroyuki Koshino; Takuto Kumano; Suresh Panthee; Tohru Dairi; Jun Ishikawa; Haruo Ikeda; Yoshiyuki Sakaki; Hiroyuki Osada
Journal:  Nat Chem Biol       Date:  2011-06-05       Impact factor: 15.040

7.  Stereocontrol of 5,5-spiroketals in the synthesis of cephalosporolide H epimers.

Authors:  Sami F Tlais; Gregory B Dudley
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

8.  Pollenopyrroside A and B, novel pyrrole ketohexoside derivatives from bee-collected Brassica campestris pollen.

Authors:  Juan-Li Guo; Zi-Ming Feng; Ya-Jun Yang; Zhi-Wu Zhang; Pei-Cheng Zhang
Journal:  Chem Pharm Bull (Tokyo)       Date:  2010-07       Impact factor: 1.645

9.  Hetero-Diels-Alder reactions of cyclic ketone derived enamide. A new and efficient concept for the asymmetric Robinson annulation.

Authors:  Florian Gallier; Hidayat Hussain; Arnaud Martel; Andreas Kirschning; Gilles Dujardin
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

10.  Stereoselective synthesis of benzannulated spiroketals: influence of the aromatic ring on reactivity and conformation.

Authors:  Guodong Liu; Jacqueline M Wurst; Derek S Tan
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005
View more
  6 in total

Review 1.  Spirocyclic derivatives as antioxidants: a review.

Authors:  Karen Acosta-Quiroga; Cristian Rojas-Peña; Luz Stella Nerio; Margarita Gutiérrez; Efraín Polo-Cuadrado
Journal:  RSC Adv       Date:  2021-06-21       Impact factor: 4.036

2.  Synthesis of the spiroiminal moiety and approaches to the synthesis of marineosins A and B.

Authors:  Xiao-Chuan Cai; Barry B Snider
Journal:  J Org Chem       Date:  2013-11-21       Impact factor: 4.354

3.  Stereocontrolled Synthesis of Spiroketals: An Engine for Chemical and Biological Discovery.

Authors:  Alyssa L Verano; Derek S Tan
Journal:  Isr J Chem       Date:  2017-03-10       Impact factor: 3.333

4.  Cascade N-Alkylation/Hemiacetalization for Facile Construction of the Spiroketal Skeleton of Acortatarin Alkaloids with Therapeutic Potentiality in Diabetic Nephropathy.

Authors:  Pei Cao; Zhen-Jie Li; Wen-Wu Sun; Shashwat Malhotra; Yuan-Liang Ma; Bin Wu; Virinder S Parmar
Journal:  Nat Prod Bioprospect       Date:  2014-12-16

5.  Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants.

Authors:  Alyssa L Verano; Derek S Tan
Journal:  Chem Sci       Date:  2017-03-15       Impact factor: 9.825

6.  Nucleotide Analogues Bearing a C2' or C3'-Stereogenic All-Carbon Quaternary Center as SARS-CoV-2 RdRp Inhibitors.

Authors:  Amarender Manchoju; Renaud Zelli; Gang Wang; Carla Eymard; Adrian Oo; Mona Nemer; Michel Prévost; Baek Kim; Yvan Guindon
Journal:  Molecules       Date:  2022-01-17       Impact factor: 4.411
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.