Format

Send to:

Choose Destination
See comment in PubMed Commons below
J Am Chem Soc. 2010 Nov 10;132(44):15559-61. doi: 10.1021/ja1082798.

Total synthesis of (+)-roxaticin via C-C bond forming transfer hydrogenation: a departure from stoichiometric chiral reagents, auxiliaries, and premetalated nucleophiles in polyketide construction.

Author information

  • 1University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, USA.

Abstract

A total synthesis of the oxo-polyene macrolide (+)-roxaticin is achieved in 20 steps from 1,3-propanediol. In this approach, 9 of 10 C-C bonds formed in the longest linear sequence are made via metal catalysis, including 7 C-C bonds formed by iridium catalyzed alcohol C-C coupling. Notably, the present synthesis, which represents the most concise preparation of any oxo-polyene macrolide reported to date, is achieved in the absence of chiral reagents and chiral auxiliaries with minimal use of premetalated C-nucleophiles.

PMID:
20961111
[PubMed - indexed for MEDLINE]
PMCID:
PMC2975273
Free PMC Article
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for American Chemical Society Icon for PubMed Central
    Loading ...
    Write to the Help Desk