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Literature DB >> 21751773

Assembly of the isoindolinone core of muironolide A by asymmetric intramolecular Diels-Alder cycloaddition.

Abstract

The hexahydro-1H-isoindolin-1-one core of muironolide A was prepared by asymmetric intramolecular Diels-Alder cycloaddition using a variant of the MacMillan organocatalyst which sets the C4,C5 and C11 stereocenters.

Entities: Chemical Species

Mesh：

Substances：

Year: 2011 PMID： 21751773 PMCID： PMC4000739 DOI： 10.1021/ol201461n

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

11 in total

1. Esmodil: an acetylcholine mimetic resurfaces in a Southern Australian marine sponge Raspailia (Raspailia) sp.

Authors: Robert J Capon; Colin Skene; Edward H Liu; Ernest Lacey; Jennifer H Gill; Kirstin Heiland; Thomas Friedel
Journal: Nat Prod Res Date: 2004-08 Impact factor: 2.861

2. Structure elucidation at the nanomole scale. 3. Phorbasides G-I from Phorbas sp.

Authors: Doralyn S Dalisay; Tadeusz F Molinski
Journal: J Nat Prod Date: 2010-04-23 Impact factor: 4.050

3. Chlorocyclopropane macrolides from the marine sponge Phorbas sp. assignment of the configurations of phorbasides A and B by quantitative CD.

Authors: Colin K Skepper; John B Macmillan; Guang-Xiong Zhou; Makoto N Masuno; Tadeusz F Molinski
Journal: J Am Chem Soc Date: 2007-03-21 Impact factor: 15.419

4. Peloruside A: a potent cytotoxic macrolide isolated from the new zealand marine sponge Mycale sp.

Authors: L M West; P T Northcote; C N Battershill
Journal: J Org Chem Date: 2000-01-28 Impact factor: 4.354

5. Cesium effect: high chemoselectivity in direct N-alkylation of amines.

Authors: Ralph Nicholas Salvatore; Advait S Nagle; Kyung Woon Jung
Journal: J Org Chem Date: 2002-02-08 Impact factor: 4.354

6. Enantioselective organocatalytic intramolecular Diels-Alder reactions. The asymmetric synthesis of solanapyrone D.

Authors: Rebecca M Wilson; Wendy S Jen; David W C Macmillan
Journal: J Am Chem Soc Date: 2005-08-24 Impact factor: 15.419

7. A tetrachloro polyketide hexahydro-1H-isoindolone, muironolide A, from the marine sponge Phorbas sp. natural products at the nanomole scale.

Authors: Doralyn S Dalisay; Brandon I Morinaka; Colin K Skepper; Tadeusz F Molinski
Journal: J Am Chem Soc Date: 2009-06-10 Impact factor: 15.419

8. NMR quantitation of natural products at the nanomole scale.

Authors: Doralyn S Dalisay; Tadeusz F Molinski
Journal: J Nat Prod Date: 2009-04 Impact factor: 4.050

9. Phorbasides A-E, cytotoxic chlorocyclopropane macrolide glycosides from the marine sponge Phorbas sp. CD determination of C-methyl sugar configurations.

Authors: John B MacMillan; Guang Xiong-Zhou; Colin K Skepper; Tadeusz F Molinski
Journal: J Org Chem Date: 2008-04-16 Impact factor: 4.354

10. Halichondrin B and homohalichondrin B, marine natural products binding in the vinca domain of tubulin. Discovery of tubulin-based mechanism of action by analysis of differential cytotoxicity data.

Authors: R L Bai; K D Paull; C L Herald; L Malspeis; G R Pettit; E Hamel
Journal: J Biol Chem Date: 1991-08-25 Impact factor: 5.157

2 in total

1. An efficient synthesis of the fully elaborated isoindolinone unit of muironolide A.

Authors: Qing Xiao; Kyle Young; Armen Zakarian
Journal: Org Lett Date: 2013-06-13 Impact factor: 6.005

Review 2. The chemistry of isoindole natural products.

Authors: Klaus Speck; Thomas Magauer
Journal: Beilstein J Org Chem Date: 2013-10-10 Impact factor: 2.883

2 in total