Use of t-butyl 4-diethylphosphono-3-oxobutanethioate for tetramic acid synthesis: Total synthesis of the plasmodial pigment fuligorubin A

✍ Scribed by Steven V. Ley; Stephen C. Smith; Peter R. Woodward

• Book ID: 104217646
• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 164 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)82204-2

✦ Synopsis

A short, efficient synthesis of the yellow slime mould pigment fuligorubin A (I) has been achieved using coupling of t-butyl4-diethylphosphono-3-oxobutanethioate with deca-2,4,6,8-tetraenal and subsequent substitution with a glutamic acid derivative followed by Dieckmann cyclisation.

The polyene acyltetramic acid fuligorubin A ( 1) is a naturally occurring pigment recently isolated from the yellow slime mould Fuligo septica (L.) Wiggers. 1 This compound is thought to be involved in photoreceptor and energy conversion processes during the life cycle of this interesting species.

HO

Here we report a concise and efficient synthesis which both confirms the absolute configuration of (1) and employs methodology developed in these laboratories for the preparation of unsaturated P-ketoamides.2>3

The amino acid fragment in (1) was readily prepared from the commercially available (R)-glutamic acid derivative (2) by a straightforward sequence of reactions involving N-methylation4 and esterification using ethereal diazomethane followed by deprotection to give (3) in 36% overall yield (Scheme 1).