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Type of Document	Dissertation
Author	Schaefer, Phillip Cuthbert
URN	etd-10032002-124237
Persistent URL	http://resolver.caltech.edu/CaltechETD:etd-10032002-124237
Title	Squalene cyclization
Degree	PhD
Option	Chemistry
Advisory Committee	Advisor Name Title Unknown Committee Member
Keywords	none
Date of Defense	1968-09-09
Availability	unrestricted
Abstract It has been observed that the proton, which is located at C-14 in squalene or C-13 in the "presterol cation," migrates less than 10% of the time (with a confidence level of 74%) to C-20 in lanosterol, and therefore 90% of the time (with a confidence level of 74%) to C-17 in lanosterol. If enzymatically controlled reactions are stereospecific, then at C-13/C17/C-20 in the "presterol cation," there are two sequential 1, 2-migrations during the backbone rearrangement to form lanosterol. A theoretical interpretation of this observation, which reflects on the stereochemistry of the C-18/C-19 double bond of squalene just prior to cyclization, is presented. A theoretical discussion of the minimal requirements for binding squalene-2, 3-oxide to an enzyme in order to obtain complete stereochemical control over the product is presented.
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