Literature DB >> 21793536

Syntheses of chloroisosulochrin and isosulochrin and biomimetic elaboration to maldoxin, maldoxone, dihydromaldoxin, and dechlorodihydromaldoxin.

Min Yu1, Barry B Snider.   

Abstract

An efficient synthesis of chloroisosulochrin was accomplished using a novel ortho-selective chlorination of a phenol with sulfuryl chloride and 2,2,6,6-tetramethylpiperidine as the key step. Further elaboration by a biomimetic route converted chloroisosulochrin to dihydromaldoxin, maldoxone (lactone formed by dehydration of dihydromaldoxin), and maldoxin and isosulochrin to dechlorodihydromaldoxin and dechloromaldoxin.
© 2011 American Chemical Society

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Year:  2011        PMID： 21793536      PMCID： PMC3206263          DOI： 10.1021/ol201561w

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


  6 in total

1.  RES-1214-1 and -2, novel non-peptidic endothelin type A receptor antagonists produced by Pestalotiopsis sp.

Authors:  T Ogawa; K Ando; Y Aotani; K Shinoda; T Tanaka; E Tsukuda; M Yoshida; Y Matsuda
Journal:  J Antibiot (Tokyo)       Date:  1995-12       Impact factor: 2.649

2.  Chloropupukeanolides C-E: cytotoxic pupukeanane chlorides with a spiroketal skeleton from Pestalotiopsis fici.

Authors:  Ling Liu; Torsten Bruhn; Liangdong Guo; Daniel C G Götz; Reto Brun; August Stich; Yongsheng Che; Gerhard Bringmann
Journal:  Chemistry       Date:  2011-02-08       Impact factor: 5.236

3.  Substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazole-6-carboxylic acids: high-ceiling diuretics with uricosuric activity.

Authors:  J J Plattner; A K Fung; J A Parks; R J Pariza; S R Crowley; A G Pernet; P R Bunnell; P W Dodge
Journal:  J Med Chem       Date:  1984-08       Impact factor: 7.446

4.  Chloropestolide A, an antitumor metabolite with an unprecedented spiroketal skeleton from Pestalotiopsis fici.

Authors:  Ling Liu; Yan Li; Shuchun Liu; Zhihui Zheng; Xulin Chen; Hua Zhang; Liangdong Guo; Yongsheng Che
Journal:  Org Lett       Date:  2009-07-02       Impact factor: 6.005

5.  Study of very reactive tautomeric phenol dienones as dienes in Diels-Alder reactions.

Authors:  Yves L Dory; Andrée-Lucie Roy; Pierre Soucy; Pierre Deslongchamps
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005

6.  Chloropupukeananin, the first chlorinated pupukeanane derivative, and its precursors from Pestalotiopsis fici.

Authors:  Ling Liu; Shuchun Liu; Lihua Jiang; Xulin Chen; Liangdong Guo; Yongsheng Che
Journal:  Org Lett       Date:  2008-03-04       Impact factor: 6.005
  6 in total
  4 in total

1.  Total syntheses of graphisin A and sydowinin B.

Authors:  Andrew Little; John A Porco
Journal:  Org Lett       Date:  2012-05-23       Impact factor: 6.005

2.  Diels-Alder reaction of maldoxin with an isopropenylallene.

Authors:  Min Yu; Barry B Snider
Journal:  Tetrahedron       Date:  2011-10-04       Impact factor: 2.457

3.  A Simple, General Synthesis of Carbonimidic Dichlorides.

Authors:  Claire M Gober; Hoang V Le; Bruce Ganem
Journal:  Tetrahedron Lett       Date:  2012-06-15       Impact factor: 2.415

4.  New 1,3-benzodioxin-4-ones from Synnemapestaloides ericacearum sp. nov., a biosynthetic link to remarkable compounds within the Xylariales.

Authors:  Joey B Tanney; Justin B Renaud; J David Miller; David R McMullin
Journal:  PLoS One       Date:  2018-06-27       Impact factor: 3.240
  4 in total

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