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Literature DB >> 25748275

Syntheses of arnottin I and arnottin II.

Matthew J Moschitto¹, David R Anthony¹, Chad A Lewis¹.

Abstract

Short total syntheses of arnottin I and II were accomplished in 5 and 6 steps, respectively. A sesamol-benzyne cycloaddition with a 3-furyl-benzoate followed by regiospecific lactonization provided rapid, large-scale access to the core of arnottin I. Saponification of arnottin I and hypervalent iodide mediated spirocyclization provided an efficient and direct preparation of racemic arnottin II.

Entities: Chemical Disease Gene Species

Mesh：

Substances：

Year: 2015 PMID： 25748275 PMCID： PMC4453770 DOI： 10.1021/acs.joc.5b00107

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

20 in total

1. Enantioselective Kita oxidative spirolactonization catalyzed by in situ generated chiral hypervalent iodine(III) species.

Authors: Muhammet Uyanik; Takeshi Yasui; Kazuaki Ishihara
Journal: Angew Chem Int Ed Engl Date: 2010-03-15 Impact factor: 15.336

2. Asymmetric Kita spirolactonisation catalysed by anti-dimethanoanthracene-based iodoarenes.

Authors: Stephen J Murray; Hasim Ibrahim
Journal: Chem Commun (Camb) Date: 2015-02-11 Impact factor: 6.222

3. Asymmetric dearomatizing spirolactonization of naphthols catalyzed by spirobiindane-based chiral hypervalent iodine species.

Authors: Toshifumi Dohi; Naoko Takenaga; Tomofumi Nakae; Yosuke Toyoda; Mikio Yamasaki; Motoo Shiro; Hiromichi Fujioka; Akinobu Maruyama; Yasuyuki Kita
Journal: J Am Chem Soc Date: 2013-03-07 Impact factor: 15.419

4. Hyperaromatic stabilization of arenium ions: acid-catalyzed dehydration of 2-substituted 1,2-dihydro-1-naphthols.

Authors: Jaya Satyanarayana Kudavalli; Dara Coyne; Rory A More O'Ferrall
Journal: J Org Chem Date: 2011-12-13 Impact factor: 4.354

5. Ruthenium-catalyzed coupling of oxabenzonorbornadienes with alkynes bearing a propargylic oxygen atom: access to stereodefined benzonorcaradienes.

Authors: Alphonse Tenaglia; Sylvain Marc; Laurent Giordano; Innocenzo De Riggi
Journal: Angew Chem Int Ed Engl Date: 2011-08-19 Impact factor: 15.336

6. Benzannulation for the regiodefined synthesis of 2-alkyl/aryl-1-naphthols: total synthesis of arnottin I.

Authors: Dipakranjan Mal; Amit Kumar Jana; Prithiba Mitra; Ketaki Ghosh
Journal: J Org Chem Date: 2011-03-31 Impact factor: 4.354

7. Combined directed remote metalation-transition metal catalyzed cross coupling strategies: the total synthesis of the aglycones of the gilvocarcins V, M, and E and arnottin I.

Authors: Clint A James; Victor Snieckus
Journal: J Org Chem Date: 2009-06-05 Impact factor: 4.354

8. Rhodium-catalyzed asymmetric cyclodimerization of oxabenzonorbornadienes and azabenzonorbornadienes: scope and limitations.

Authors: Anna Allen; Paul Le Marquand; Ryan Burton; Karine Villeneuve; William Tam
Journal: J Org Chem Date: 2007-09-20 Impact factor: 4.354

Syntheses of arnottin I and arnottin II.

1. Enantioselective Kita oxidative spirolactonization catalyzed by in situ generated chiral hypervalent iodine(III) species.

2. Asymmetric Kita spirolactonisation catalysed by anti-dimethanoanthracene-based iodoarenes.

3. Asymmetric dearomatizing spirolactonization of naphthols catalyzed by spirobiindane-based chiral hypervalent iodine species.

4. Hyperaromatic stabilization of arenium ions: acid-catalyzed dehydration of 2-substituted 1,2-dihydro-1-naphthols.

5. Ruthenium-catalyzed coupling of oxabenzonorbornadienes with alkynes bearing a propargylic oxygen atom: access to stereodefined benzonorcaradienes.

6. Benzannulation for the regiodefined synthesis of 2-alkyl/aryl-1-naphthols: total synthesis of arnottin I.

7. Combined directed remote metalation-transition metal catalyzed cross coupling strategies: the total synthesis of the aglycones of the gilvocarcins V, M, and E and arnottin I.

8. Rhodium-catalyzed asymmetric cyclodimerization of oxabenzonorbornadienes and azabenzonorbornadienes: scope and limitations.

9. Enantiopure 1,4-benzoxazines via 1,2-cyclic sulfamidates. Synthesis of levofloxacin.

10. Isomerization of 7-oxabenzonorbornadienes into naphthols catalyzed by [RuCl(2)(CO)(3)](2).

1. Photocatalytic Oxidative Dearomatization of Orcinaldehyde Derivatives.

Review 2. Synthesis of spirocyclic scaffolds using hypervalent iodine reagents.

Review 3. Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis.