𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of a marine polyether toxin, okadaic acid (2) — synthesis of segment b

✍ Scribed by Yoshiyasu Ichikawa; Minoru Isobe; Toshio Goto

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
919 KB
Volume
43
Category
Article
ISSN
0040-4020

No coin nor oath required. For personal study only.

✦ Synopsis

The central synthetic segment B for okadeic acid comprises the carbons from 15 through 27 including 6 asymmetric carbons. Its synthesis started from a D-Glucose derivative, whose carbon was extended twice for the six and five membered etherial ring formation. The original conformation of the sugar was inverted when the Spiro-ether was formed to eventuate the axial aldehyde formation in 35 overall steps.

📜 SIMILAR VOLUMES

Synthesis of a marine polyether toxin, o
Synthesis of a marine polyether toxin, okadaic acid [4]p1 -- total synthesis
✍ Minoru Isobe; Yoshiyasu Ichikawa; Dong-Lu Bai; Hisanori Masaki; Toshio Goto 📂 Article 📅 1987 🏛 Elsevier Science 🌐 French ⚖ 888 KB

## 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

Synthetic studies toward marine toxic po
Synthetic studies toward marine toxic polyethers (2) synthesis of the B-segment of okadaic acid and coupling with the C-segment
✍ Yoshiyasu Ichikawa; Minoru Isobe; Toshio Goto 📂 Article 📅 1984 🏛 Elsevier Science 🌐 French ⚖ 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