Abstract
AbstractThe absolute configurations of the two algal pheromones multifidene 1 and viridiene 2 were determined as (+)‐(3S, 4S)‐3‐[(Z)‐1‐butenyl]‐4‐vinylcyclopentene and (+)‐(3R, 4S)‐3‐[(1Z)‐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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