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PMID: 17629295 Published · ppublish English Journal Article Research Support, N.I.H., Extramural

Total synthesis of herboxidiene/GEX 1A.

Organic letters ·Vol. 9 ·No. 16 ·2007-08-02 ·Pages 3141-3

Zhang Y, Panek JS

Abstract

A convergent enantioselective synthesis of herboxidiene/GEX 1A (1) is described that features a double stereodifferentiating crotylation, [4 + 2] annulation, and a silicon-based sp2-sp2 cross-coupling to assemble the conjugated diene.

MeSH Terms
Antineoplastic Agents/chemical synthesis,chemistry,pharmacology Fatty Alcohols/chemical synthesis,chemistry,pharmacology Molecular Structure Pyrans/chemical synthesis,chemistry,pharmacology Stereoisomerism Streptomyces/chemistry
Chemicals
Antineoplastic Agents Fatty Alcohols Pyrans herboxidiene
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Zhang Yun
Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Panek James S
References (10)
10 references, click to expand
  1. Sequential silylcarbocyclization/silicon-based cross-coupling reactions.
    J Am Chem Soc. 2007 Mar 28;129(12):3737-44 PMID: 17335205
  2. Stereocontrolled [4+2]-annulation accessing dihydropyrans: synthesis of the C1a-C10 fragment of kendomycin.
    Org Lett. 2005 Apr 14;7(8):1529-32 PMID: 15816744
  3. Reactions of alkenylchromium reagents prepared from alkenyl trifluoromethanesulfonates (triflates) with chromium(II) chloride under nickel catalysis.
    J Am Chem Soc. 1986 Sep 1;108(19):6048-50 PMID: 22175376
  4. GEX1 compounds, novel antitumor antibiotics related to herboxidiene, produced by Streptomyces sp. I. Taxonomy, production, isolation, physicochemical properties and biological activities.
    J Antibiot (Tokyo). 2002 Oct;55(10):855-62 PMID: 12523818
  5. Fluoride-promoted cross-coupling reactions of alkenylsilanols. Elucidation of the mechanism through spectroscopic and kinetic analysis.
    J Am Chem Soc. 2004 Apr 21;126(15):4865-75 PMID: 15080691
  6. A stereodivergent approach to chiral nonracemic N-protected alpha,alpha-dialkylated amino acids.
    J Am Chem Soc. 2003 Oct 8;125(40):12106-7 PMID: 14518992
  7. Dinuclear asymmetric Zn aldol additions: formal asymmetric synthesis of fostriecin.
    J Am Chem Soc. 2005 Mar 23;127(11):3666-7 PMID: 15771479
  8. Ruthenium-catalyzed vinylsilane synthesis and cross-coupling as a selective approach to alkenes: benzyldimethylsilyl as a robust vinylmetal functionality.
    Org Lett. 2003 May 29;5(11):1895-8 PMID: 12762680
  9. A qualitative examination of the effects of silicon substituents on the efficiency of cross-coupling reactions.
    J Org Chem. 2006 Oct 27;71(22):8500-9 PMID: 17064026
  10. GEX1 compounds, novel antitumor antibiotics related to herboxidiene, produced by Streptomyces sp. II. The effects on cell cycle progression and gene expression.
    J Antibiot (Tokyo). 2002 Oct;55(10):863-72 PMID: 12523819
Article Info
Journal
Organic letters
Abbr.
Org Lett
ISSN
1523-7060
Published
2007-08-02
Epub
2007-00-13
Pages
3141-3
Language
English
Region
United States
NLM ID
100890393
PMCID
PMC3164305
Subset
IM
Grants
NIGMS NIH HHS · R01 GM055740 · United States
NIGMS NIH HHS · R01 GM055740-07 · United States
NIGMS NIH HHS · GM55740 · United States
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