Synthesis and evaluation of cephalostatin 1 analogs
Abstract
This thesis will describe a new method to functionalize C-18 angular methyl of hecogenin acetate 1.1. A concise and practical route has been completed leading to the syntheses of several South 1 analogs. Four of them were coupled with North 1 subunit to furnish the corresponding Cephalostatin 1 analogs (1.2, 1.3, 1.4 and 1.5, Figure 1.10). Their cytotoxicities which were obtained in a NCI 10 cell line minipanel will be reported in Chapter 4. Some application and new methodology developments are covered in Chapter 2 and 3: (1) dyotropic rearrangement of a 7-membered lactone to a 6-ring spiro lactone; (2) PPSE promoted Friedel-Crafts reaction on nonaromatic acids; (3) epoxidation reactions using dioxiranes derived from tetrafluoroacetophenones.
Degree
Ph.D.
Advisors
Fuchs, Purdue University.
Subject Area
Organic chemistry|Pharmacology
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