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Stereoselective total syntheses of (±)-sinularene and of (±)-5-epi-sinularene via intramolecular type-I-“magnesium-ene” reaction

✍ Scribed by Wolfgang Oppolzer; Heinrich F. Strauss; Dana P. Simmons

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
212 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

+)-Sinularene (l_) as well as (+)-5-epi-sinularene

(2) were synthesised in a stereocontrolled manner from the norbornene 2 in overall yields of 4% and 8%, respectively.

The key step 5 + 6 involves a reqio-and stereoselective intramolecular "magnesium-ene" reaction.

📜 SIMILAR VOLUMES

Application of the intramolecular magnes
Application of the intramolecular magnesium-ene reaction to the stereocontrolled total syntheses of (±)-12-acetoxysinularene and (±)-5-epi-12-acetoxysinularene
✍ Wolfgang Oppolzer; Tadhg Begley; Alison Ashcroft 📂 Article 📅 1984 🏛 Elsevier Science 🌐 French ⚖ 208 KB

The sesquiterpene (+)-12-acetoxysinularene (1) and its C(5)-epimer 13 were each synthesized stereoselectively from the norbo&yl-iodoacetal 1 in 5%and 7% overall yields. The critical step 10 -t 11 involves the regio-and stereo--selective "magnesium-ene" reaction 5 -t 2.

Total synthesis of (±)-Δ9(12)-capnellene
Total synthesis of (±)-Δ9(12)-capnellene via iterative intramolecular type-I-“Magnesium-ene” reactions
✍ Wolfgang Oppolzer; Kurt Bättig 📂 Article 📅 1982 🏛 Elsevier Science 🌐 French ⚖ 224 KB

The marine triquinane sesquiterpene A 9(12) -capnellene (1) was synthesised from 2,2,5-trimethyl-5-hexenal (2) by a sequence of 11 synthetic operations \_ in 5% overall yield. The key steps 3 + 4 + 5 -f 6 involve two intramolecular type-I-"Mg-ene" processes.