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Published December 10, 2003 | Supplemental Material
Journal Article Open

The Total Synthesis of (−)-Lemonomycin


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.

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.

Attached Files

Supplemental Material - ja039223qsi20031024_062744.ci

Supplemental Material - ja039223qsi20031024_062744.cif

Supplemental Material - ja039223qsi20031024_062759.ci

Supplemental Material - ja039223qsi20031024_062759.cif

Supplemental Material - ja039223qsi20031103_074727.pd

Supplemental Material - ja039223qsi20031103_074727.pdf


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