Studies Directed at the Synthesis of Optically Active Pretazettine via Intramolecular Nitrone/Alkene Cycloaddition Reactions

Journal Article (Journal Article)

A protocol for the synthesis of optically active pretazettine which focuses on both the control of relative stereochemistry between the angular aryl and C6a hydroxyl groups and absolute stereochemistry has been developed and executed. The synthesis of the 1,3-dithiane ketal of (Z)-ethyl 3-(1,3-benzodioxol-5-yl)-5,7-dioxo-2-heptanoate is described. Treatment of this alkene aldehyde with N-(α-methylbenzyl)hydroxylamine afforded a nitrone, which underwent intramolecular 1,3-dipolar cycloaddition to afford the two diastereomeric isoxazolidine cycloadducts in a 16:1 ratio. The sense of chirality transfer was determined by a single-crystal X-ray analysis of the major isomer. © 1991, American Chemical Society. All rights reserved.

Full Text

Duke Authors

Cited Authors

  • Baldwin, SW; McPhail, AT; Aubé, J

Published Date

  • November 1, 1991

Published In

Volume / Issue

  • 56 / 23

Start / End Page

  • 6546 - 6550

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo00023a019

Citation Source

  • Scopus