Synthetic studies on (-) lemonomycin: construction of the tetracyclic core
Date
2013
Authors
Jiménez-Somarribas, Alberto, author
Williams, Robert M., advisor
Wood, John L., committee member
Shi, Yian, committee member
Ladanyi, Branka M., committee member
Crick, Dean C., committee member
Journal Title
Journal ISSN
Volume Title
Abstract
Documented herein are efforts towards the asymmetric total synthesis of (-)-lemonomycin, a member of the tetrahydroisoquinoline antitumor antibiotics family of natural products. We describe a concise route for the assembly of the tetracyclic core of this molecule, which involves a Pictet-Spengler reaction for the construction of the tetrahydroisoquinoline fragment and an azomethine ylide [3+2] dipolar cycloaddition for the construction of the diazabicyclo[3.2.1]octane ring system. The above-described synthetic efforts, while not totally successful, provide the basis for the future completion of the total synthesis of this natural product and other related compounds.
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Subject
[3+2] dipolar cycloaddition
Pictet-Spengler reaction
Lemonomycin
asymmetric synthesis