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Stereoselective Aldol Condensations via Boron Enolates. The Syntheses of (+)-Prelog-Djerassi Lactone and (+)-Tylonolide

Citation

Bartroli, Javier Francisco (1984) Stereoselective Aldol Condensations via Boron Enolates. The Syntheses of (+)-Prelog-Djerassi Lactone and (+)-Tylonolide. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/3v27-xh37. https://resolver.caltech.edu/CaltechTHESIS:11092018-094859390

Abstract

The use of boron enolates of chiral N-acyl oxazolidinones i and ii in highly stereoselective aldol condensations is described. Mild base hydrolysis of the products affords optically pure erythro β-hydroxy acids and the chiral auxiliary, which can be reconverted into i or ii in one step.

The utility and scope of these reactions is demonstrated by the total syntheses of (+)-Prelog-Djerassi lactone and (+)-Tylonolide, cyclic 5,20-hemiacetal .

[Chemical structures included in scanned thesis' abstract, p. v.]

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):
  • Dougherty, Dennis A.
Thesis Committee:
  • Evans, David A. (chair)
  • Collins, Terrence J.
  • Dervan, Peter B.
  • Dougherty, Dennis A.
Defense Date:9 December 1983
Record Number:CaltechTHESIS:11092018-094859390
Persistent URL:https://resolver.caltech.edu/CaltechTHESIS:11092018-094859390
DOI:10.7907/3v27-xh37
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/ja00398a058DOIArticle adapted for Chapter I.
https://doi.org/10.1016/s0040-4039(00)86954-3DOIArticle adapted for Chapter II.
https://doi.org/10.1016/s0040-4039(00)85658-0DOIArticle adapted for Chapter II.
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:11268
Collection:CaltechTHESIS
Deposited By: Lisa Fischelis
Deposited On:09 Nov 2018 19:17
Last Modified:16 Apr 2021 23:15

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