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Synthetic studies toward marine toxic polyethers [5] the total synthesis of okadaic acid

✍ Scribed by Minoru Isobe; Yoshiyasu Ichikawa; Toshio Goto

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
262 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

The total synthesis of okadaic acid has been accomplished through the coupling of all the segments, A, B and C, by means of sulfone-carbanion strategy.

[CX]D t13.7' (C'

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✍ Yoshiyasu Ichikawa; Minoru Isobe; Toshio Goto πŸ“‚ Article πŸ“… 1984 πŸ› Elsevier Science 🌐 French βš– 259 KB

Part of okadaic acid la vas synthesized stereoselectively in the fora of 4a (involving C-16 through C-38 uith 10 asymaetric carbons), by coupling the equivalents of 2 and 3 as the synthetic segments Il and C (Scheme 1). the forser being prepared via 12 and 6 froa a D-glucopyranose derivative (Scheae

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## 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