eprintid: 25623
rev_number: 23
userid: 1419
dir: disk0/00/02/56/23
datestamp: 2015-07-22 13:52:34
lastmod: 2021-06-12 22:55:59
status_changed: 2015-07-22 13:52:33
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Wipf, P
creators_name: Coish, PDG
creators_email: pwipf@pitt.edu
creators_email: 
creators_id: PWIPF
creators_id: 
title: Total synthesis of (±)-nisamycin
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
abstract: We have developed a highly convergent synthesis of the manumycin-type m- C7N-antibiotic nisamycin that is applicable to other members of this family of antibiotics. The synthesis features a three-step sequence to the epoxyquinol core that serves as a scaffold for the attachment of the polyene side chains. The eastern polyene side chain was constructed via a novel organozirconocene-mediated synthesis. Zirconocene methodology was also applied to the synthesis of the polyene side chains of asukamycin. The southern side chain of nisamycin was introduced via a Stille reaction that employed a vinyl bromo ketone, derived from an acid-sensitive bromo ketal. Pd-mediated coupling of the vinyl bromide with a stannyl TIPS ester gave TIPS-protected nisamycin that was readily converted to the natural product.
date: 1999-07-09
date_type: published
publication: Journal of Organic Chemistry
volume: 64
number: 14
pagerange: 5053 - 5061
refereed: TRUE
issn: 0022-3263
id_number: 10.1021/jo990413m
citation:   Wipf, P and Coish, PDG  (1999) Total synthesis of (±)-nisamycin.  Journal of Organic Chemistry, 64 (14).  5053 - 5061.  ISSN 0022-3263     
document_url: http://d-scholarship-dev.library.pitt.edu/25623/1/licence.txt