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Short Syntheses of (±)‐Grandisol and (±) Lineatin via , a common Intermediate
Author(s) -
AljancicSolaja Ivana,
Rey Max,
Dreiding André S.
Publication year - 1987
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.19870700510
Subject(s) - chemistry , saponification , ketone , bicyclic molecule , adduct , acetone , ring (chemistry) , organic chemistry , medicinal chemistry
A 6‐step synthesis of (±)‐grandisol ( 1 ) is presented, which involves dichloroketene addition to 3‐methyl‐3‐butenyl acetate ( 4 ), reductive dechlorination of the adduct 6 to the ketone 7 and saponification to 8 , aldolization of 7 or 8 with acetone and cyclization to the bicyclic ketone 9 , Wolff‐kishner , reduction to 14 , and finally ring opening to 1. Since 9 is a known intermediate of the synthesis of (±)‐lineatin ( 2 ), the latter can now be obtained in 6 steps.