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Literature DB >> 19222082

Parallel kinetic resolution approach to the cyathane and cyanthiwigin diterpenes using a cyclopropanation/Cope rearrangement.

Laura C Miller¹, J Maina Ndungu, Richmond Sarpong.

Abstract

Parallel effort: Stereodivergent parallel kinetic resolution of a racemic mixture of dienes using Davies' [Rh(2){(S)-dosp}(4)] or [Rh(2){(R)-dosp}(4)] catalysts promotes a tandem vinyl diazoacetate cyclopropanation/Cope rearrangement sequence to afford two diastereomeric, enantioenriched cycloheptadienes, which correspond to the natural antipodes of the title diterpenoids (see scheme).

Entities: Chemical Disease Species

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Year: 2009 PMID： 19222082 PMCID： PMC3342692 DOI： 10.1002/anie.200806154

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

11 in total

1. Parallel Kinetic Resolutions.

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Journal: Angew Chem Int Ed Engl Date: 2000-03 Impact factor: 15.336

2. Parallel kinetic resolution of racemic mixtures: a new strategy for the preparation of enantiopure compounds?

Authors: Juan R Dehli; Vicente Gotor
Journal: Chem Soc Rev Date: 2002-11 Impact factor: 54.564

3. Direct synthesis of (+)-erogorgiaene through a kinetic enantiodifferentiating step.

Authors: Huw M L Davies; Abbas M Walji
Journal: Angew Chem Int Ed Engl Date: 2005-03-04 Impact factor: 15.336

4. The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation.

Authors: John A Enquist; Brian M Stoltz
Journal: Nature Date: 2008-06-26 Impact factor: 49.962

5. Scabronine G-methylester enhances secretion of neurotrophic factors mediated by an activation of protein kinase C-zeta.

Authors: Y Obara; H Kobayashi; T Ohta; Y Ohizumi; N Nakahata
Journal: Mol Pharmacol Date: 2001-05 Impact factor: 4.436

6. Cyathin, a new antibiotic complex produced by Cyathus helenae.

Authors: A D Allbutt; W A Ayer; H J Brodie; B N Johri; H Taube
Journal: Can J Microbiol Date: 1971-11 Impact factor: 2.419

7. Discovery and optimization of anthranilic acid sulfonamides as inhibitors of methionine aminopeptidase-2: a structural basis for the reduction of albumin binding.

Authors: George S Sheppard; Jieyi Wang; Megumi Kawai; Steve D Fidanze; Nwe Y BaMaung; Scott A Erickson; David M Barnes; Jason S Tedrow; Lawrence Kolaczkowski; Anil Vasudevan; David C Park; Gary T Wang; William J Sanders; Robert A Mantei; Fabio Palazzo; Lora Tucker-Garcia; Pingping Lou; Qian Zhang; Chang H Park; Ki H Kim; Andrew Petros; Edward Olejniczak; David Nettesheim; Phillip Hajduk; Jack Henkin; Richard Lesniewski; Steven K Davidsen; Randy L Bell
Journal: J Med Chem Date: 2006-06-29 Impact factor: 7.446

8. Total synthesis of (+)-cyanthiwigin U.

Authors: Matthew W B Pfeiffer; Andrew J Phillips
Journal: J Am Chem Soc Date: 2005-04-20 Impact factor: 15.419

9. Total synthesis of (+)-cyanthiwigin AC.

Authors: T Jagadeeswar Reddy; Guillaume Bordeau; Laird Trimble
Journal: Org Lett Date: 2006-11-23 Impact factor: 6.005

10. Conversion of cyanthiwigin U to related cyanthiwigins: total syntheses of cyanthiwigin W and cyanthiwigin Z.

Authors: Matthew W B Pfeiffer; Andrew J Phillips
Journal: Tetrahedron Lett Date: 2008-11-24 Impact factor: 2.415

14 in total

Review 1. Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors: Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal: Angew Chem Int Ed Engl Date: 2014-03-03 Impact factor: 15.336

2. Regiodivergent reactions through catalytic enantioselective silylation of chiral diols. Synthesis of sapinofuranone A.

Authors: Jason M Rodrigo; Yu Zhao; Amir H Hoveyda; Marc L Snapper
Journal: Org Lett Date: 2011-06-28 Impact factor: 6.005

3. Catalyst-controlled formal [4 + 3] cycloaddition applied to the total synthesis of (+)-barekoxide and (-)-barekol.

Authors: Yajing Lian; Laura C Miller; Stephen Born; Richmond Sarpong; Huw M L Davies
Journal: J Am Chem Soc Date: 2010-09-08 Impact factor: 15.419

4. Highly stereoselective C-C bond formation by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and chiral allylic alcohols.

Authors: Zhanjie Li; Brendan T Parr; Huw M L Davies
Journal: J Am Chem Soc Date: 2012-06-25 Impact factor: 15.419

5. Divergent outcomes of carbene transfer reactions from dirhodium- and copper-based catalysts separately or in combination.

Authors: Xinfang Xu; Wen-Hao Hu; Peter Y Zavalij; Michael P Doyle
Journal: Angew Chem Int Ed Engl Date: 2011-10-06 Impact factor: 15.336

6. Asymmetric Syntheses of the Flavonoid Diels-Alder Natural Products Sanggenons C and O.

Authors: Chao Qi; Yuan Xiong; Vincent Eschenbrenner-Lux; Huan Cong; John A Porco
Journal: J Am Chem Soc Date: 2016-01-19 Impact factor: 15.419

Review 7. Application of donor/acceptor-carbenoids to the synthesis of natural products.

Authors: Huw M L Davies; Justin R Denton
Journal: Chem Soc Rev Date: 2009-09-30 Impact factor: 54.564

8. Finding Opportunities from Surprises and Failures. Development of Rhodium-Stabilized Donor/Acceptor Carbenes and Their Application to Catalyst-Controlled C-H Functionalization.

Authors: Huw M L Davies
Journal: J Org Chem Date: 2019-10-10 Impact factor: 4.354

9. Biomimetic kinetic resolution: highly enantio- and diastereoselective transfer hydrogenation of aglain ketones to access flavagline natural products.

Authors: Steven D Stone; Neil J Lajkiewicz; Luke Whitesell; Ahmed Hilmy; John A Porco
Journal: J Am Chem Soc Date: 2014-12-29 Impact factor: 15.419

10. Acylammonium salts as dienophiles in Diels-Alder/lactonization organocascades.

Authors: Mikail E Abbasov; Brandi M Hudson; Dean J Tantillo; Daniel Romo
Journal: J Am Chem Soc Date: 2014-03-12 Impact factor: 15.419