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Literature DB >> 22084899

Gram-scale synthesis of the A'B'-subunit of angelmicin B.

Benjamin C Milgram¹, Brian B Liau, Matthew D Shair.

Abstract

A gram-scale enantiospecific synthesis of the A'B'-subunit of angelmicin B is reported. The synthesis involves a Lewis acid catalyzed contrasteric Diels-Alder reaction and a tandem silyl zincate 1,6-addition/enolate oxidation sequence.

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Year: 2011 PMID： 22084899 PMCID： PMC3237735 DOI： 10.1021/ol202728v

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

21 in total

1. Studies toward the total synthesis of angelmicin B (hibarimicin B): synthesis of a model CD-D' arylnaphthoquinone.

Authors: Sridhar Narayan; William R Roush
Journal: Org Lett Date: 2004-10-14 Impact factor: 6.005

2. Tandem catalysis for a one-pot regioselective protection of carbohydrates: the example of glucose.

Authors: Antoine Français; Dominique Urban; Jean-Marie Beau
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

3. Assignment and stereocontrol of hibarimicin atropoisomers.

Authors: Ian M Romaine; Jonathan E Hempel; Ganesh Shanmugam; Hiroshi Hori; Yasuhiro Igarashi; Prasad L Polavarapu; Gary A Sulikowski
Journal: Org Lett Date: 2011-08-03 Impact factor: 6.005

4. Signal transduction inhibitors, hibarimicins A, B, C, D and G produced by Microbispora. II. Structural studies.

Authors: H Hori; Y Igarashi; T Kajiura; T Furumai; K Higashi; T Ishiyama; M Uramota; Y Uehara; T Oki
Journal: J Antibiot (Tokyo) Date: 1998-04 Impact factor: 2.649

5. Synthesis of an A'B' Precursor to Angelmicin B: Product Diversification in the Suárez Lactol Fragmentation.

Authors: Jialiang Li; Louis Todaro; David R Mootoo
Journal: European J Org Chem Date: 2011-09-07

6. Biosynthesis of hibarimicins. III. Structures of new hibarimicin-related metabolites produced by blocked mutants.

Authors: Yasuhiro Igarashi; Takayuki Kajiura; Tamotsu Furumai; Hiroshi Hori; Kazuaki Higashi; Tadayuki Ishiyama; Masakazu Uramoto; Yoshimasa Uehara; Toshikazu Oki
Journal: J Antibiot (Tokyo) Date: 2002-01 Impact factor: 2.649

7. Studies into the stereoselectivity of tartrate-derived dienophiles.

Authors: Wei-Der Lee; Kwangho Kim; Gary A Sulikowski
Journal: Org Lett Date: 2005-04-28 Impact factor: 6.005

8. Asymmetric construction of rings A-D of daphnicyclidin-type alkaloids.

Authors: Travis B Dunn; J Michael Ellis; Christiane C Kofink; James R Manning; Larry E Overman
Journal: Org Lett Date: 2009-12-17 Impact factor: 6.005

9. Signal transduction inhibitors, hibarimicins, A, B, C, D and G produced by Microbispora. I. Taxonomy, fermentation, isolation and physico-chemical and biological properties.

Authors: T Kajiura; T Furumai; Y Igarashi; H Hori; K Higashi; T Ishiyama; M Uramoto; Y Uehara; T Oki
Journal: J Antibiot (Tokyo) Date: 1998-04 Impact factor: 2.649