The Total Synthesis of Brevetoxin B: A Twelve‐Year Odyssey in Organic Synthesis

Abstract

AbstractThe total synthesis of brevetoxin B has been achieved recently after a long search for a suitable pathway. This twelve‐year odysseyThe Odyssey of Homer, translated by R. Lattimore, Harper Perenial, New York, 1975. Homer's Odyssey, one of the western world's first two poems (the Iliad is the other), is the tale of the adventures, wanderings, and exploits of Odysseus, a Greek hero of the Trojan war, as he attempts to reach Ithaca, his home island where his wife Penelope awaits him. During his journey Odysseus has an incredible series of adventures and setbacks caused by the anger of the god Poseidon, whose son Odysseus had blinded. Finally, assisted by his patroness, the goddess Athene, Odysseus returns home to Ithaca to find and punish the suitors, evil men who tried to win his wife's hand and who squandered his wealth and corrupted his servants while he was away. Telemachus, Odysseus' son, who had his own share of adventures while growing up, facing the suitors and, looking for his father, joins him in glory and wisdom as they reestablish their throne on Ithaca. Besides Odysseus, other main characters of Odyssey are as follows:Telemachus: The son of Odysseus, who is just entering manhood, is highly conscious of his duties as a prince successor to the throne and protector of his mother as well as the need to live up to his father's reputation as a hero. His actions waver between the immature and the well‐thought over as he searches for the truth about his father and desperately appeals to others for help. It is not until towards the end of the story that he exhibits great courage, skills, and confidence and one feels that he is, indeed, the son of Odysseus.Athene: She is the daughter of Zeus, goddess of wisdom, and patroness of arts and crafts. Odysseus is her favorite and protegé and she is his heroine, even though she is a goddess. She plays a leading role in all important events in the narrative, and her spirit and power always influence and assist Odysseus and Telemachus in their difficult moments. A friend and a confidant to Odysseus, she enjoys winning him over and her relationship with him, while the hero adores her and finds special comfort, companionship, and understanding in her.Poseidon: Younger brother to Zeus, god of the sea and of earthquakes, father of Polyphenus the one‐eyed Cyclops whom Odysseus blinds. As a ruler of the sea and natural phenomena, Poseidon is able to place many obstacles in front of Odysseus, whom he despises. Poseidon, however, is unable to hold out against the combined pressure of the other gods, particularly Athene, of whom Odysseus is a favorite, and so eventually relents, but not before he repeatedly unleashes his anger.The Cyclops, Scylla, and The Sirens: Some of the superhuman and monstrous characters of the tale who inflicted tremendous tortures and blows at Odysseus and his men, before he finally overcame them.The Suitors: The evil noblemen of Ithaca who attempt to undermine Odysseus, win the hand of his queen, Penelope, and corrupt his palace servants. They succeed partly, wasting away a great deal of Odysseus fortune, but he eventually prevails and punishes them.Ithaca: The island kingdom of Odysseus, most likely located somewhere off the western coast of Greece and the destination of the hero in this adventure. It is interesting to compare places, events, and characters from the Odyssey to those of modern‐day total synthesis, an excercise left to the imagination of the reader! in synthetic organic chemistry was marked by several strategic and tactical routes, and resulted in numerous new synthetic methods. This article is a behind‐thescenes account of the total synthesis of brevetoxin B, from its origins at the University of Pennsylvania to its completion at the University of California, San Diego, and The Scripps Research Institute, La Jolla, California.