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Synthesis of a marine polyether toxin, okadaic acid [4]p1 -- total synthesis

✍ Scribed by Minoru Isobe; Yoshiyasu Ichikawa; Dong-Lu Bai; Hisanori Masaki; Toshio Goto

Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 888 KB
Volume: 43
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)86918-0

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✦ Synopsis

Abetract

Three segments A, B and C for okadaic acid synthesis were coupled with each other in the order of At(BtC), the key steps of the twice couplings being between sulfone carbanions and aldehydea. After the BtC coupling, the asymmetric center C-27 was generated by a hydride reduction of the corresponding ketone 16 under electronic control. The second coupling was followed to form the C-14/15 double bond. Oxidation of the Q-oxy aldehyde 36 into the carboxylic acid group was achieved with sodium chlorite without Cl/C-Z bond cleavage. The total syntheeis of okadaic acid was accomplished in 106 steps from commercially available D-glucose derivatives and butyne-diol.

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