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Total Synthesis of β-Chamigrene


Dow, William Clinton (1982) Total Synthesis of β-Chamigrene. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/6kmn-mt31.


A total synthesis of the sesquiterpene (±)-β-Chamigrene is described. A key step is the preparation of spiroketone ii through Claisen rearrangement of the vinyl-substituted cycloheptapyran i. A modified Meinwald-Cava ring contraction sequence is used for the intramolecular elaboration of a functionalized one-carbon unit at the hindered alpha flank of the spirocycle. This procedure affords ester iii. Alternate reaction pathways available to the reactive ketene intermediate are also discussed. These results are compared with observations made in a previously reported synthesis of aphidicolin.

[Chemical structure included in scanned thesis' abstract, p. iv.]

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):
  • Grubbs, Robert H.
Thesis Committee:
  • Grubbs, Robert H. (chair)
  • Ireland, Robert E.
  • Anson, Fred C.
  • Dougherty, Dennis A.
Defense Date:4 January 1982
Funding AgencyGrant Number
Record Number:CaltechTHESIS:05142018-155247666
Persistent URL:
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:10882
Deposited By: Mel Ray
Deposited On:15 May 2018 18:12
Last Modified:19 Apr 2021 22:30

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