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Literature DB >> 18844364

A concise and modular synthesis of pyranicin.

Abstract

A modular, 13-step synthesis of the tetrahydropyran-containing annonaceous acetogenin pyranicin is reported. Key features are the use of an Achmatowicz oxidation-Kishi reduction sequence for the assembly of a pyranone from a furan and the application of Fu's alkyl-alkyl Suzuki coupling for subunit union.

Entities: Chemical Disease Gene Species

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Year: 2008 PMID： 18844364 PMCID： PMC2901595 DOI： 10.1021/ol802041c

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

17 in total

1. A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes.

Authors: N K Anand; E M Carreira
Journal: J Am Chem Soc Date: 2001-10-03 Impact factor: 15.419

Review 2. Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action.

Authors: Almudena Bermejo; Bruno Figadere; Maria-Carmen Zafra-Polo; Isabel Barrachina; Ernesto Estornell; Diego Cortes
Journal: Nat Prod Rep Date: 2005-03-15 Impact factor: 13.423

3. Highly functionalized pyranopyrans from furans: a synthesis of the C27-C38 and C44-C53 subunits of norhalichondrin B.

Authors: James A Henderson; Katrina L Jackson; Andrew J Phillips
Journal: Org Lett Date: 2007-11-14 Impact factor: 6.005

4. Chemical Synthesis of the GHIJKLMNO Ring System of Maitotoxin.

Authors: K C Nicolaou; Michael O Frederick; Antonio C B Burtoloso; Ross M Denton; Fatima Rivas; Kevin P Cole; Robert J Aversa; Romelo Gibe; Taiki Umezawa; Takahiro Suzuki
Journal: J Am Chem Soc Date: 2008-05-16 Impact factor: 15.419

5. Synthetic studies on (2R,4'R,8'R)-alpha-tocopherol. Facile syntheses of optically active, saturated, acyclic isoprenoids via stereospecific [3,3]sigmatropic rearrangements.

Authors: K K Chan; N Cohen; J P De Noble; A C Specian; G Saucy
Journal: J Org Chem Date: 1976-10-29 Impact factor: 4.354

6. Total synthesis of a cytotoxic acetogenin, pyranicin.

Authors: Shunya Takahashi; Akemi Kubota; Tadashi Nakata
Journal: Org Lett Date: 2003-04-17 Impact factor: 6.005

7. Room-temperature alkyl-alkyl Suzuki cross-coupling of alkyl bromides that possess beta hydrogens.

Authors: M R Netherton; C Dai; K Neuschütz; G C Fu
Journal: J Am Chem Soc Date: 2001-10-17 Impact factor: 15.419

8. Total synthesis of pyranicin.

Authors: Daniel Strand; Tobias Rein
Journal: Org Lett Date: 2005-01-20 Impact factor: 6.005

9. Synthesis and assignment of the absolute configuration of the anti-Helicobacter pylori agents CJ-12,954 and CJ-13,014.

Authors: Margaret A Brimble; Christina J Bryant
Journal: Org Biomol Chem Date: 2007-07-31 Impact factor: 3.876

10. Origin of stereoselectivity in the reduction of a planar oxacarbenium.

Authors: Joann M Um; K N Houk; Andrew J Phillips
Journal: Org Lett Date: 2008-07-23 Impact factor: 6.005

11 in total

Review 1. Transition metal-catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry.

Authors: Junwon Choi; Gregory C Fu
Journal: Science Date: 2017-04-14 Impact factor: 47.728

2. PALLADIUM-CATALYZED ALKYL-ALKYL SUZUKI CROSS-COUPLINGS OF PRIMARY ALKYL BROMIDES AT ROOM-TEMPERATURE: (13-CHLOROTRIDECYLOXY)TRIETHYLSILANE [Silane, [(13-chlorotridecyl)oxy]triethyl-].

Authors: Sha Lou; Gregory C Fu; Takuyo Higo; Tohru Fukuyama
Journal: Organic Synth Date: 2010-01-01

3. Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.

Authors: Arun K Ghosh; Margherita Brindisi
Journal: RSC Adv Date: 2016-11-24 Impact factor: 3.361

4. Stereoconvergent amine-directed alkyl-alkyl Suzuki reactions of unactivated secondary alkyl chlorides.

Authors: Zhe Lu; Ashraf Wilsily; Gregory C Fu
Journal: J Am Chem Soc Date: 2011-05-10 Impact factor: 15.419

5. Alkyl-alkyl Suzuki cross-coupling of unactivated secondary alkyl chlorides.

Authors: Zhe Lu; Gregory C Fu
Journal: Angew Chem Int Ed Engl Date: 2010-09-03 Impact factor: 15.336

6. The palladium-catalyzed anti-Markovnikov hydroalkylation of allylic alcohol derivatives.

Authors: Ryan J DeLuca; Matthew S Sigman
Journal: Org Lett Date: 2012-12-19 Impact factor: 6.005

7. One-pot catalytic asymmetric synthesis of pyranones.

Authors: Kevin Cheng; Ann Rowley Kelly; Rachel A Kohn; Jessica F Dweck; Patrick J Walsh
Journal: Org Lett Date: 2009-06-18 Impact factor: 6.005

8. Enantioconvergent cross-couplings of racemic alkylmetal reagents with unactivated secondary alkyl electrophiles: catalytic asymmetric Negishi α-alkylations of N-Boc-pyrrolidine.

Authors: Christopher J Cordier; Rylan J Lundgren; Gregory C Fu
Journal: J Am Chem Soc Date: 2013-07-19 Impact factor: 15.419

9. Asymmetric total synthesis of pyranicin.

Authors: Michael T Crimmins; Danielle L Jacobs
Journal: Org Lett Date: 2009-06-18 Impact factor: 6.005

10. Stereospecific nickel-catalyzed cross-coupling reactions of benzylic ethers and esters.

Authors: Emily J Tollefson; Luke E Hanna; Elizabeth R Jarvo
Journal: Acc Chem Res Date: 2015-07-21 Impact factor: 22.384