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The Total Synthesis of (−)-Lemonomycin

Ashley, Eric R. and Cruz, Ernest G. and Stoltz, Brian M. (2003) The Total Synthesis of (−)-Lemonomycin. Journal of the American Chemical Society, 125 (49). pp. 15000-15001. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170216-075818295

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Abstract

The first total synthesis of the novel glycosylated tetrahydroisoquinoline antitumor antibiotic (−)-lemonomycin has been accomplished (15 steps from 9). The highly convergent synthesis relies on a key asymmetric dipolar cycloaddition to set the stereochemistry of the aglycone core, a Suzuki fragment coupling to connect the diazabicycle to the aryl subunit, and a stereoselective Pictet−Spengler reaction that incorporates the aminoglycoside subunit directly into the core structure without the need for late-stage glycosylation or protecting group manipulations. The novel aminoglycoside was prepared using a highly diastereoselective Felkin-controlled acetate aldol addition reaction to a threonine-derived ketone.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja039223qDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja039223qPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja039223qRelated ItemSupporting Information
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2003 American Chemical Society. Received 24 October 2003. Published online 14 November 2003. Published in print 1 December 2003. This work is dedicated to Professor E. J. Corey on the occasion of his 75th birthday. The authors are grateful to Caltech, the University of California TRDRP (predoctoral fellowship to E.R.A.), and the J. Irvine Foundation (predoctoral fellowship to E.G.C.) for financial support. We also thank T. Y. Lam for experimental assistance and Dr. H. He (Wyeth-Ayerst) for an authentic sample of (−)-1.
Funders:
Funding AgencyGrant Number
CaltechUNSPECIFIED
California Tobacco-Related Disease Research ProgramUNSPECIFIED
James Irvine FoundationUNSPECIFIED
Issue or Number:49
Record Number:CaltechAUTHORS:20170216-075818295
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170216-075818295
Official Citation:The Total Synthesis of (−)-Lemonomycin Eric R. Ashley, Ernest G. Cruz, and Brian M. Stoltz Journal of the American Chemical Society 2003 125 (49), 15000-15001 DOI: 10.1021/ja039223q
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:74361
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:16 Feb 2017 17:05
Last Modified:03 Oct 2019 16:37

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