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The First Total Synthesis of (–)-Lemonomycin and Progress toward the Total Synthesis of (+)-Cyanocycline A

Citation

Ashley, Eric Robert (2006) The First Total Synthesis of (–)-Lemonomycin and Progress toward the Total Synthesis of (+)-Cyanocycline A. Dissertation (Ph.D.), California Institute of Technology. http://resolver.caltech.edu/CaltechETD:etd-11152005-155011

Abstract

The first total synthesis of (–)-lemonomycin has been accomplished. The synthesis features a novel, auxiliary-controlled asymmetric dipolar cycloaddition, a highly convergent Suzuki coupling, a diastereoselective enamide hydrogenation to set the C(3) stereochemistry, and a convergent, efficient, and completely diastereoselective Pictet-Spengler cyclization with a glycosyloxy acetaldehyde.

The total synthesis of (+)-cyanocycline A has been approached along two routes. Both routes feature dipolar cycloaddition reactions with alkyne-containing substrates and completely diastereoselective hydrogenations to set the C(4) stereochemistry. Proposals for the advancement of late-stage intermediates to the natural product are included.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Antibiotic; Antitumor; Dipolar Cycloaddition; Pictet-Spengler; Tetrahydroisoquinoline; Total Synthesis
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Awards:Tobacco-Related Disease Research Program (TRDRP) Dissertation Award, 2002
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Stoltz, Brian M.
Thesis Committee:
  • Grubbs, Robert H. (chair)
  • Stoltz, Brian M.
  • MacMillan, David W. C.
  • Gray, Harry B.
Defense Date:31 October 2005
Record Number:CaltechETD:etd-11152005-155011
Persistent URL:http://resolver.caltech.edu/CaltechETD:etd-11152005-155011
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:4579
Collection:CaltechTHESIS
Deposited By: Imported from ETD-db
Deposited On:17 Nov 2005
Last Modified:23 Jan 2017 21:49

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