5-Bromopentadienal: a versatile intermediate for the synthesis of functionalized polyenic compounds

Abstract

5-Bromopentadienal I b ( n = 2), easily obtained from the potassium glutaconaldehyde salt, is used as precursor of o-bromoheptatrienal Id, o-bromomethoxyhexatriene 2, diene diols 4, diene diones 5, 1,6-dibrornohexa-l,3,5-triene 6 and 1,8 triene diol 8, of controlled configuration.

Synthetic methodologies for carbo-substituted conjugated dienes

“…However, the most widely used synthons of this type are electrophilic reagents such as 5-bromopenta-2,4-dienal (426), 386,387 5-dimethylaminopenta-2,4-dienal (427) 388 and ethyl 5-(butyltelluro)penta-2,4-dienoate (428). 389 Substitution of alkyl groups for the electronegative elements (Br, NMe 2 and BuTe) in these compounds is accomplished by means of organometallic reagents.…”

Stereocontrolled Total Synthesis of (−)‐Aurisides A and B

“…Synthesis of the C8-C17 subunit 7 (Scheme 3) commenced with the bromination of potassium glutaconaldehyde (13), [11] according to the method of Duhamel and co-workers. [12] Treatment of 13 with Br 2 and PPh 3 provided the corresponding E,E bromodienal 14 (68 %). The stage was now set for the critical AVM reaction between 14 and silyl dienolate 15 [13] to introduce the C13 stereocenter, along with the 10E-trisubstituted alkene functionality.…”

Palladium Catalyzed Cross-Coupling Reaction of Functional Organozinc Reagents with (2E,4E)- and (2E,4Z)-5-Bromopenta-2,4-dienals: Easy Access to Functional Conjugated Dienic Aldehydes

“…In the preliminary note, [2] reactions were conducted with simple organozinc reagents. In this article, we report an extension of this palladium catalyzed cross-coupling reaction using various functional organozinc reagents 3 with (2E,4E ) dienal 1 and its (2E,4Z ) isomer 2, [3] without any protection of the aldehydic function.…”