A Short and Efficient Synthesis of (±)‐Modhephene by a Stereoelectronically‐Controlled Ene‐Reaction | Zendy

Oppolzer Wolfgang | Zendy; Bättig Kurt | Zendy

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A Short and Efficient Synthesis of (±)‐Modhephene by a Stereoelectronically‐Controlled Ene‐Reaction

Author(s) -

Oppolzer Wolfgang,

Bättig Kurt

Publication year - 1981

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19810640756

Subject(s) - chemistry , ene reaction , yield (engineering) , intramolecular force , propellane , combinatorial chemistry , stereochemistry , medicinal chemistry , bicyclic molecule , materials science , metallurgy

(±)‐Modhephene ( 6 ) has been synthesized from the easily available trimethylpentalenone 1 in 6 steps in 26% overall yield (Scheme 2) . The remarkably smooth 1,4‐addition/enolate trapping 1 → 2 and subsequent selenoxide elimination after oxidation furnished the key intermediate 3 which underwent an expedient and highly stereoselctive intramolecular ene ‐reaction to give the propellane 4 , readily convertible to (±)‐ 6 .

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