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Literature DB >> 23550898

General synthetic approach to functionalized dihydrooxepines.

K C Nicolaou¹, Ruocheng Yu, Lei Shi, Quan Cai, Min Lu, Philipp Heretsch.

Abstract

A three-step sequence to access functionalized 4,5-dihydrooxepines from cyclohexenones has been developed. This approach features a regioselective Baeyer-Villiger oxidation and subsequent functionalization via the corresponding enol phosphate intermediate.

Entities: Chemical Gene

Mesh：

Substances：
Cyclohexanones
Oxepins

Year: 2013 PMID： 23550898 PMCID： PMC3653422 DOI： 10.1021/ol4006689

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

14 in total

1. Synthesis and biological evaluation of epidithio-, epitetrathio-, and bis-(methylthio)diketopiperazines: synthetic methodology, enantioselective total synthesis of epicoccin G, 8,8'-epi-ent-rostratin B, gliotoxin, gliotoxin G, emethallicin E, and haematocin and discovery of new antiviral and antimalarial agents.

Authors: K C Nicolaou; Min Lu; Sotirios Totokotsopoulos; Philipp Heretsch; Denis Giguère; Ya-Ping Sun; David Sarlah; Thu H Nguyen; Ian C Wolf; Donald F Smee; Craig W Day; Selina Bopp; Elizabeth A Winzeler
Journal: J Am Chem Soc Date: 2012-10-04 Impact factor: 15.419

2. Structure elucidation of sesquiterpene dilactones from Mikania scandens (L.) Willd.

Authors: W Herz; P S Subramaniam; P S Santhanam; K Aota; A L Hall
Journal: J Org Chem Date: 1970-05 Impact factor: 4.354

3. Synthesis and stereochemistry of occidenol, a 4,5-dihydrooxipin-containing sesquiterpene: a pericyclic approach.

Authors: John N Marx; Abdulaziz Ajlouni
Journal: Nat Prod Commun Date: 2010-01 Impact factor: 0.986

4. Oxepinochromenones, furochromenone, and their putative precursors from the endolichenic fungus Coniochaeta sp.

Authors: Yinchao Wang; Zhihui Zheng; Shuchun Liu; Hua Zhang; Erwei Li; Liangdong Guo; Yongsheng Che
Journal: J Nat Prod Date: 2010-05-28 Impact factor: 4.050

5. Enantioselective total synthesis of (-)-acetylaranotin, a dihydrooxepine epidithiodiketopiperazine.

Authors: Julian A Codelli; Angela L A Puchlopek; Sarah E Reisman
Journal: J Am Chem Soc Date: 2011-10-28 Impact factor: 15.419

6. A unified strategy targeting the thiodiketopiperazine mycotoxins exserohilone, gliotoxin, the epicoccins, the epicorazines, rostratin A and aranotin.

Authors: Ulrike Gross; Martin Nieger; Stefan Bräse
Journal: Chemistry Date: 2010-08-31 Impact factor: 5.236

7. Functionalized oxepines via fragmentation of highly strained epoxides.

Authors: Andrew J Leyhane; Marc L Snapper
Journal: Org Lett Date: 2006-11-09 Impact factor: 6.005

8. Role of the gem-difluoro moiety in the tandem ring-closing metathesis-olefin isomerization: regioselective preparation of unsaturated lactams.

Authors: Santos Fustero; María Sanchez-Roselló; Diego Jiménez; Juan F Sanz-Cervera; Carlos Del Pozo; José Luis Aceña
Journal: J Org Chem Date: 2006-03-31 Impact factor: 4.354

6. Stereoselective tandem iridium-catalyzed alkene isomerization-cope rearrangement of ω-diene epoxides: efficient access to acyclic 1,6-dicarbonyl compounds.

Authors: Rahul Suresh; Itai Massad; Ilan Marek
Journal: Chem Sci Date: 2021-06-09 Impact factor: 9.825

6 in total

General synthetic approach to functionalized dihydrooxepines.

2. Structure elucidation of sesquiterpene dilactones from Mikania scandens (L.) Willd.

3. Synthesis and stereochemistry of occidenol, a 4,5-dihydrooxipin-containing sesquiterpene: a pericyclic approach.

4. Oxepinochromenones, furochromenone, and their putative precursors from the endolichenic fungus Coniochaeta sp.

5. Enantioselective total synthesis of (-)-acetylaranotin, a dihydrooxepine epidithiodiketopiperazine.

6. A unified strategy targeting the thiodiketopiperazine mycotoxins exserohilone, gliotoxin, the epicoccins, the epicorazines, rostratin A and aranotin.

7. Functionalized oxepines via fragmentation of highly strained epoxides.

8. Role of the gem-difluoro moiety in the tandem ring-closing metathesis-olefin isomerization: regioselective preparation of unsaturated lactams.

9. Synthesis of dihydrooxepin models related to the antitumor antibiotic MPC1001.

10. Asymmetric synthesis of the ABC-ring system of the antitumor antibiotic MPC1001.

1. Synthesis of 1,2-dihydro-2-oxo-4-quinolinyl phosphates from 2-acyl-benzoic acids.

2. Migratory Aptitudes in Rearrangements of Destabilized Vinyl Cations.

Review 3. Rearrangements of organic peroxides and related processes.

4. Total Synthesis of Oxepin and Dihydrooxepin Containing Natural Products.

5. Enantioselective Synthesis of (-)-Acetylapoaranotin.

6. Stereoselective tandem iridium-catalyzed alkene isomerization-cope rearrangement of ω-diene epoxides: efficient access to acyclic 1,6-dicarbonyl compounds.