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Absolute Configuration of Multifidene and Viridiene, the Sperm Releasing and Attracting Pheromones of Brown Algae

✍ Scribed by Wilhelm Boland; Karin Mertes; Lothar Jaenicke; Dieter G. Müller; Elsbet Fölster

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
501 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The absolute configurations of the two algal pheromones multifidene 1 and viridiene 2 were determined as (+)‐(3__S__, 4__S__)‐3‐[(Z)‐1‐butenyl]‐4‐vinylcyclopentene and (+)‐(3__R__, 4__S__)‐3‐[(1__Z__)‐1, 3‐butadienyl]‐4‐vinylcyclopentene, respectively. The strategy involves enzyme‐initiated asymmetric synthesis of the ring‐saturated pheromone analogues (+)‐8a and (−)‐8b and their subsequent catalytic hydrogenation to the chiral cycloalkanes 9a and 9b, only the letter of which is also obtained from the two natural messengers (+)‐1 or (+)‐2. Biological activity assays proved these enantiomers of 1 or 2 to be the characteristic pheromones for male gametes of the seaweeds Syringoderma, Cutleria multifida and Chorda tomentosa.

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