en
Scientific article
English

A Concise Synthesis of (E)- and (Z)-Neomanoalides

Published inHelvetica chimica acta, vol. 77, no. 3, p. 661-667
Publication date1994
Abstract

The first synthesis of (Z)-neomanoalide (4) and an improved synthesis of its (E)-isomer 3 was accomplished in a concise, regiocontrolled manner by exploiting 2-[(tert-butyl)dimethylsiloxy]-4{[(tert-butyl)dimethylsiloxy]-methyl}furan (6) as the key reagent. Lithiation of 6 and subsequent reaction with the (2Z)- or (2E)-isomer of (6E)-3-{[(tert-butyl)dimethylsiloxy]methyl}-7-methyl-9-(2′,6′,6′-trimethylcyclohex-1′-enyl)nona-2,6-dienyl bromide (5), followed by hydrolysis, afforded the corresponding neomanoalide.

Citation (ISO format)
JEFFORD, Charles et al. A Concise Synthesis of (E)- and (Z)-Neomanoalides. In: Helvetica chimica acta, 1994, vol. 77, n° 3, p. 661–667. doi: 10.1002/hlca.19940770309
Main files (1)
Article (Published version)
accessLevelRestricted
Identifiers
ISSN of the journal0018-019X
455views
1downloads

Technical informations

Creation06/21/2016 2:44:00 PM
First validation06/21/2016 2:44:00 PM
Update time03/15/2023 12:29:19 AM
Status update03/15/2023 12:29:19 AM
Last indexation01/16/2024 9:08:18 PM
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack