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Absolute Configuration of Multifidene and Viridiene, the Sperm Releasing and Attracting Pheromones of Brown Algae
Author(s) -
Boland Wilhelm,
Mertes Karin,
Jaenicke Lothar,
Müller Dieter G.,
Fölster Elsbet
Publication year - 1983
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19830660632
Subject(s) - sex pheromone , chemistry , stereochemistry , enantiomer , absolute configuration , pheromone , ring (chemistry) , botany , organic chemistry , biology
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 .