Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: application to the synthesis of the C(23)-C(40) fragment of tetrafibricin

Jeremy Kister; Philippe Nuhant; Ricardo Lira; Achim Sorg; William R Roush

doi:10.1021/ol2003836

Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: application to the synthesis of the C(23)-C(40) fragment of tetrafibricin

Org Lett. 2011 Apr 1;13(7):1868-71. doi: 10.1021/ol2003836. Epub 2011 Mar 4.

Authors

Jeremy Kister¹, Philippe Nuhant, Ricardo Lira, Achim Sorg, William R Roush

Affiliation

¹ Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, United States.

Abstract

A highly stereoselective synthesis of (E)-1,5-syn-diols 6 is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-syn-diols 6 in 72-98% yields with >95% ee and >20:1 dr. Application of this method to the synthesis of the tetrafibricin C(23)-C(40) fragment 19 is described.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Kinetics
Macrolides / chemistry*
Molecular Structure
Stereoisomerism

Substances

Macrolides
tetrafibricin

Abstract

Publication types

MeSH terms

Substances

Grants and funding