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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 .