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Enantioselective synthesis of the AB-ring system of the antitumor antibiotic tetrazomine

Wipf, P and Hopkins, CR (2001) Enantioselective synthesis of the AB-ring system of the antitumor antibiotic tetrazomine. Journal of Organic Chemistry, 66 (9). 3133 - 3139. ISSN 0022-3263

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Abstract

The synthesis of the 1,2,3,4-tetrahydroisoquinoline moiety of tetrazomine was accomplished in 18 steps and in 3% overall yield from commercially available o-anisaldehyde. The reaction sequence utilizes a Sharpless asymmetric dihydroxylation to install the stereocenter and an intramolecular Friedel-Crafts hydroxyalkylation with an N-protected 2-oxo-acetamide to close the heterocyclic ring.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Hopkins, CR
Date: 4 May 2001
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 66
Number: 9
Page Range: 3133 - 3139
DOI or Unique Handle: 10.1021/jo015512q
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Alkylation; Antibiotics, Antineoplastic--chemical synthesis; Antibiotics, Antineoplastic--chemistry; Hydroxylation; Indicators and Reagents; Piperidines--chemical synthesis; Piperidines--chemistry; Stereoisomerism
Other ID: 10.1021/jo015512q
PubMed ID: 11325279
Date Deposited: 13 Feb 2014 23:17
Last Modified: 30 Oct 2017 23:57
URI: http://d-scholarship-dev.library.pitt.edu/id/eprint/20493

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