Literature DB >> 19894740

Synthesis of the cores of hypocrellin and shiraiachrome: diastereoselective 1,8-diketone aldol cyclization.

Erin M O'Brien1, Jingxian Li, Patrick J Carroll, Marisa C Kozlowski.   

Abstract

Intramolecular 1,8-diketone aldol reactions were studied as a tool for the construction of the seven-membered rings of hypocrellin and shiraiachrome. Conditions were identified to obtain the relative stereochemistries present in the two natural products with excellent diastereoselectivity. In addition, a nine-membered ring congener, which has yet to be observed in nature, formed with high selectivity when a hindered amine was used in conjunction with silazide bases.

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Year:  2010        PMID： 19894740      PMCID： PMC2798919          DOI： 10.1021/jo9018914

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


  14 in total

1.  Diastereoselective cobalt-catalyzed aldol and Michael cycloreductions.

Authors:  T G Baik; A L Luis; L C Wang; M J Krische
Journal:  J Am Chem Soc       Date:  2001-05-30       Impact factor: 15.419

Review 2.  Biaryls in nature: a multi-facetted class of stereochemically, biosynthetically, and pharmacologically intriguing secondary metabolites.

Authors:  G Bringmann; C Günther; M Ochse; O Schupp; S Tasler
Journal:  Fortschr Chem Org Naturst       Date:  2001

3.  Highly enantioselective organocatalysis of the Hajos-Parrish-Eder-Sauer-Wiechert reaction by the beta-amino acid cispentacin.

Authors:  Stephen G Davies; Ruth L Sheppard; Andrew D Smith; James E Thomson
Journal:  Chem Commun (Camb)       Date:  2005-06-30       Impact factor: 6.222

4.  Antiviral activities of photoactive perylenequinones.

Authors:  J B Hudson; V Imperial; R P Haugland; Z Diwu
Journal:  Photochem Photobiol       Date:  1997-02       Impact factor: 3.421

5.  Photodynamic-induced apoptosis of human nasopharyngeal carcinoma cells using Hypocrellins.

Authors:  S M Ali; M Olivo; G Y Yuen; S K Chee
Journal:  Int J Oncol       Date:  2001-09       Impact factor: 5.650

6.  Photoinactivation of virus infectivity by hypocrellin A.

Authors:  J Hirayama; K Ikebuchi; H Abe; K W Kwon; Y Ohnishi; M Horiuchi; M Shinagawa; K Ikuta; N Kamo; S Sekiguchi
Journal:  Photochem Photobiol       Date:  1997-11       Impact factor: 3.421

7.  Synthesis of 3-epi-6,7-dideoxyxestobergsterol A.

Authors:  Y Kaji; T Koami; A Nakamura; Y Fujimoto
Journal:  Chem Pharm Bull (Tokyo)       Date:  2000-10       Impact factor: 1.645

8.  A new general route to thiophenophanes: synthesis and properties of [n](2,5)thiophenophane-1,n-diones.

Authors:  Yuji Miyahara
Journal:  J Org Chem       Date:  2006-08-18       Impact factor: 4.354

9.  Photodynamic inhibitory effects of three perylenequinones on human colorectal carcinoma cell line and primate embryonic stem cell line.

Authors:  Lan Ma; Hong Tai; Cong Li; Yu Zhang; Ze-Hua Wang; Wei-Zhi Ji
Journal:  World J Gastroenterol       Date:  2003-03       Impact factor: 5.742

10.  Lithium hexamethyldisilazide-mediated enolizations: influence of triethylamine on E/Z selectivities and enolate reactivities.

Authors:  Peter F Godenschwager; David B Collum
Journal:  J Am Chem Soc       Date:  2008-06-17       Impact factor: 15.419
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  2 in total

1.  Structural reassignment of a marine metabolite from a binaphthalenetetrol to a tetrabrominated diphenyl ether.

Authors:  Erin E Podlesny; Marisa C Kozlowski
Journal:  J Nat Prod       Date:  2012-06-12       Impact factor: 4.050

2.  Structural Diversity of Perylenequinones Is Driven by Their Redox Behavior.

Authors:  Zeinab Y Al Subeh; Amy L Waldbusser; Huzefa A Raja; Cedric J Pearce; Kin Lok Ho; Michael J Hall; Michael R Probert; Nicholas H Oberlies; Shabnam Hematian
Journal:  J Org Chem       Date:  2022-01-25       Impact factor: 4.198
  2 in total

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