A total synthesis of (−)-reiswigin a via sequential claisen rearrangement-intramolecular ester enolate alkylation
✍ Scribed by Deukjoon Kim; Kye Jung Shin; Ik Yoen Kim; Sang Woo Park
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 220 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
Ester-enolate Claisen rearrangement of 2-cycloalkenyl the biologically active RS,SR-diastereomers selectively.
The brominated terpene (+)-oppositol (1) has been synthesized utilizing a novel doubly diastereodifferentiating "folding & allylic strain-controlled' intramolecular ester enolate alkylation.
An enantioselective route to the C(1) -C(6) erythronolide unit 10 is described, involving the dioxanone-to-dihydropyran enolate Claisen rearrangement (7 + 8), regio-and stereoselective hydroboration to give 9a, and reductive fragmentation of the heterocyclic template (9c + 10). The stereocontrolled