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3: Interesting facts from the world of organic chemistry – Dienes and polyenes: Fucoserratene, Ektokarpene and Multifidene
Articles Interesting facts from the world of organic chemistry
3: Interesting facts from the world of organic chemistry – Dienes and polyenes: Fucoserratene, Ektokarpene and Multifidene
Articles Interesting facts from the world of organic chemistry

3: Interesting facts from the world of organic chemistry – Dienes and polyenes: Fucoserratene, Ektokarpene and Multifidene

Interesting facts from the world of organic chemistry

Dienes and polyenes:
Fucoserraten, ectocarpen and multifidene.

The group of dienes and polyenes includes hydrocarbons that contain two or more double bonds in their skeleton. Rather lesser known examples are multifidene together with fucoserratene and ectocarpen. These three compounds are sex pheromones produced by certain brown seaweeds.

Dieny a polyeny - 1
Fukoserrtaten, Ektokarpen a (+)-(3S,4S)-multifiden

An example of the synthesis of (+)-(3S,4S)-multifidene and its very close compound (+)-(3R,4S)-viridiene (which contains one terminal double bond in addition to multifidene) is shown in the scheme below.

Dieny a polyeny - 2
Schéma syntézy (+)-(3S,4S)-multifidenu. Vedlejším produktem je (+)-(3R,4S)-viridien.

Picture above: Scheme of the synthesis of (+)-(3S,4S)-multifidene. The byproduct is (+)-(3R,4S)-viridien.

Sources:

1) MCMURRY J.: Organic Chemistry, Seventh Edition. Copyright © 2008, 2004 Brooks/Cole, a division of Thomson Learning, Inc. Kapitola 6 – Alkenes: Structure and Reactivity, page 208.

2) LEBRETON J., V. ALPHAND a R. FURSTOSS: A Short Chemoenzymatic Synthesis of (+)-Multifidene and (+)-Viridiene. Groupe de Chimie Organique et Bioorganique,  associé au CNRS,  Faculté des Sciences de Luminy, Case 901,  163, av.  de Luminy, F – 13288 Marseille Cedex 9, France.