Literature DB >> 24777757

Enantioselective total synthesis of (-)-lansai B and (+)-nocardioazines A and B.

Haoxuan Wang1, Sarah E Reisman.   

Abstract

The concise total syntheses of the bis(pyrroloindolines) (-)-lansai B and (+)-nocardioazines A and B are reported. The key pyrroloindoline building blocks are rapidly prepared by enantioselective formal [3+2] cycloaddition reactions. The macrocycle of (+)-nocardioazine A is constructed by an unusual intramolecular diketopiperazine formation.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cycloaddition; heterocycles; macrocycles; natural products; total synthesis

Mesh：

Substances：

Year:  2014        PMID： 24777757      PMCID： PMC4086423          DOI： 10.1002/anie.201402571

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  10 in total

1.  Total synthesis and absolute configuration of nocardioazine B.

Authors:  Mingzhong Wang; Xiangyang Feng; Liangzhen Cai; Zhengshuang Xu; Tao Ye
Journal:  Chem Commun (Camb)       Date:  2012-03-23       Impact factor: 6.222

2.  Enantioselective synthesis of pyrroloindolines by a formal [3 + 2] cycloaddition reaction.

Authors:  Lindsay M Repka; Jane Ni; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

3.  Nocardioazines: a novel bridged diketopiperazine scaffold from a marine-derived bacterium inhibits P-glycoprotein.

Authors:  Ritesh Raju; Andrew M Piggott; Xiao-Cong Huang; Robert J Capon
Journal:  Org Lett       Date:  2011-04-22       Impact factor: 6.005

4.  Phenserine regulates translation of beta -amyloid precursor protein mRNA by a putative interleukin-1 responsive element, a target for drug development.

Authors:  K T Shaw; T Utsuki; J Rogers; Q S Yu; K Sambamurti; A Brossi; Y W Ge; D K Lahiri; N H Greig
Journal:  Proc Natl Acad Sci U S A       Date:  2001-06-12       Impact factor: 11.205

5.  Ligand-controlled palladium-catalyzed regiodivergent Suzuki-Miyaura cross-coupling of allylboronates and aryl halides.

Authors:  Yang Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2013-07-12       Impact factor: 15.419

6.  Synthesis of symmetrical trisubstituted olefins by cross metathesis.

Authors:  Arnab K Chatterjee; Daniel P Sanders; Robert H Grubbs
Journal:  Org Lett       Date:  2002-05-30       Impact factor: 6.005

7.  Chaetocin: a promising new antimyeloma agent with in vitro and in vivo activity mediated via imposition of oxidative stress.

Authors:  Crescent R Isham; Jennifer D Tibodeau; Wendy Jin; Ruifang Xu; Michael M Timm; Keith C Bible
Journal:  Blood       Date:  2006-11-07       Impact factor: 22.113

8.  Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

Authors:  Lindsay M Repka; Sarah E Reisman
Journal:  J Org Chem       Date:  2013-12-02       Impact factor: 4.354

9.  Direct, Enantioselective Synthesis of Pyrroloindolines and Indolines From Simple Indole Derivatives.

Authors:  Jane Ni; Haoxuan Wang; Sarah E Reisman
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

Review 10.  Amide bond formation: beyond the myth of coupling reagents.

Authors:  Eric Valeur; Mark Bradley
Journal:  Chem Soc Rev       Date:  2008-12-04       Impact factor: 54.564
  10 in total
  15 in total

1.  Lithium bis-catechol borate as an effective reductive quencher in photoredox catalysis.

Authors:  Martin J Sevrin; Laura Furst; John D Nguyen; James L Collins; Corey R J Stephenson
Journal:  Tetrahedron       Date:  2018-04-18       Impact factor: 2.457

2.  Enantioselective Total Syntheses of Akuammiline Alkaloids (+)-Strictamine, (-)-2(S)-Cathafoline, and (-)-Aspidophylline A.

Authors:  Jesus Moreno; Elias Picazo; Lucas A Morrill; Joel M Smith; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419

3.  A Mild and General Larock Indolization Protocol for the Preparation of Unnatural Tryptophans.

Authors:  Kangway V Chuang; Madeleine E Kieffer; Sarah E Reisman
Journal:  Org Lett       Date:  2016-09-06       Impact factor: 6.005

4.  Evaluation of the photodecarbonylation of crystalline ketones for the installation of reverse prenyl groups on the pyrrolidinoindoline scaffold.

Authors:  Jordan J Dotson; Neil K Garg; Miguel A Garcia-Garibay
Journal:  Tetrahedron       Date:  2020-04-10       Impact factor: 2.457

5.  Synthesis of Aza-Rocaglates via ESIPT-Mediated (3+2) Photocycloaddition.

Authors:  Wenyu Wang; Regina Cencic; Luke Whitesell; Jerry Pelletier; John A Porco
Journal:  Chemistry       Date:  2016-07-15       Impact factor: 5.236

6.  A Panel of TrpB Biocatalysts Derived from Tryptophan Synthase through the Transfer of Mutations that Mimic Allosteric Activation.

Authors:  Javier Murciano-Calles; David K Romney; Sabine Brinkmann-Chen; Andrew R Buller; Frances H Arnold
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-11       Impact factor: 15.336

7.  Bioinspired Brønsted Acid-Promoted Regioselective Tryptophan Isoprenylations.

Authors:  Tushar M Khopade; Kalyani Ajayan; Swapnil S Joshi; Amy L Lane; Rajesh Viswanathan
Journal:  ACS Omega       Date:  2021-04-12

Review 8.  Bacterial terpenome.

Authors:  Jeffrey D Rudolf; Tyler A Alsup; Baofu Xu; Zining Li
Journal:  Nat Prod Rep       Date:  2021-05-26       Impact factor: 15.111

9.  Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies.

Authors:  Elias Picazo; Lucas A Morrill; Robert B Susick; Jesus Moreno; Joel M Smith; Neil K Garg
Journal:  J Am Chem Soc       Date:  2018-05-15       Impact factor: 15.419

10.  Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration.

Authors:  Michele Mari; Simone Lucarini; Francesca Bartoccini; Giovanni Piersanti; Gilberto Spadoni
Journal:  Beilstein J Org Chem       Date:  2014-08-26       Impact factor: 2.883
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.