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I. Synthesis of dl-cis-Tetrahydroeremophilone. II. Studies on Systems Free from Angular Strain


Murayama, Stanley Tetsu (1969) I. Synthesis of dl-cis-Tetrahydroeremophilone. II. Studies on Systems Free from Angular Strain. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/EF19-GE34.


I. The total synthesis of racemic cis-tetrahydroeremophilone (17) has been achieved. The key feature of the synthesis was a solvolytic cyclization that proceeded through a symmetrical cation 41 and gave rise to two major products, one of which had the stereochemistry required for the synthesis of tetrahydroeremophilone.

II. Attempts on the synthesis of the alcohol 1 have been investigated in three related reaction sequences (Schemes 1, 4, 5, and 6). Although none of the reaction sequences gave the desired alcohol 1 that was intended for use in a solvolysis study, an unexpected product, the keto acetate 48, resulted in one sequence and afforded adamantanone (44) upon chromatography on alumina.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Chemistry
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Brown, Morris (advisor)
  • Chan, David C. (co-advisor)
Thesis Committee:
  • Unknown, Unknown
Defense Date:14 June 1968
Funding AgencyGrant Number
Record Number:CaltechTHESIS:03232017-140452739
Persistent URL:
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:10102
Deposited By: Benjamin Perez
Deposited On:24 Mar 2017 14:53
Last Modified:21 Dec 2019 04:12

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