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Synthesis of (±)-7,8-Epoxy-4-basmen-6-one by a Transannular Cyclization Strategy


Condroski, Kevin Ronald (1994) Synthesis of (±)-7,8-Epoxy-4-basmen-6-one by a Transannular Cyclization Strategy. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/svsh-y716.


The first synthesis of the cembranoid natural product (±)-7,8-epoxy-4-basmen-6-one (1) is described. Key steps of the synthetic route include the cationic cyclization of the acid chloride from 15 to provide the macrocycle 16, and the photochemical transannular radical cyclization of the ester 41 to form the tricyclic product 50. Product 50 was transformed into 1 in ten steps. Transition-state molecular modeling studies were found to provide accurate predictions of the structural and stereochemical outcomes of cyclization reactions explored experimentally in the development of the synthetic route to 1. These investigations should prove valuable in the development of transannular cyclization as a strategy for synthetic simplification.

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):
  • Myers, Andrew G.
Thesis Committee:
  • Unknown, Unknown
Defense Date:6 December 1993
Record Number:CaltechTHESIS:04292013-162401827
Persistent URL:
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:7646
Deposited By: Benjamin Perez
Deposited On:30 Apr 2013 15:39
Last Modified:16 Apr 2021 22:26

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