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Acid‐Catalysed Cyclisation of p ‐Mentha‐1,8(9)‐diene‐ and p ‐Mentha‐1,8(10)‐diene‐9‐carboxylic Acid. Novel Access to the Bicyclo[3.2.1]octane Skeleton
Author(s) -
Giersch Wolfgang,
Brauchli Robert,
Thommen Walter,
SchulteElte Karl H.
Publication year - 1986
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.19860690506
Subject(s) - bicyclic molecule , chemistry , diene , yield (engineering) , octane , ketone , bridged compounds , tricyclic , stereochemistry , medicinal chemistry , organic chemistry , natural rubber , materials science , metallurgy
Treatment of the title compounds with either H 3 PO 4 or BF 3 · Et 2 O affords the bridged tricyclic lactones 3 and 7 as main products (57 and 70% yield, resp.). This is an efficient and novel access to specifically functionalised molecules possesing the bicyclo[3.2.1]octane skeleton. Lactones 4 and 5 and the bicyclic ketone 6 were formed as by‐products (2, 7, and 10% yield, resp.).
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