Total synthesis of narbonolide and biotransformation to pikromycin

Lakshmanan Venkatraman, Christine E. Salomon, David H. Sherman, Robert A. Fecik

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

An improved total synthesis of narbonolide and its biotransformation to pikromycin is reported. This total synthesis utilized an intramolecular Nozaki-Hiyama-Kishi coupling that significantly improved macrocyclization yields (90-96%) and allowed for differentiation of the C3- and C5-oxidation states. A pikAI deletion mutant of Streptomyces venezuelae was used to biotransform synthetic narbonolide to pikromycin by glycosylation and oxidation in vivo. This integration of synthetic chemistry and engineered biotransformations holds great promise for the synthesis of novel macrolide analogues of biological interest.

Original languageEnglish (US)
Pages (from-to)9853-9856
Number of pages4
JournalJournal of Organic Chemistry
Volume71
Issue number26
DOIs
StatePublished - Dec 22 2006

Fingerprint Dive into the research topics of 'Total synthesis of narbonolide and biotransformation to pikromycin'. Together they form a unique fingerprint.

Cite this