
%0 Journal Article
%A Cambie, RC 
%A Crump, DR 
%A Duve, RN 
%T Chemistry of the Podocarpaceae. XXII. Aspects of the chemistry of Totara-8,11,13-trien-13-ol
%J Australian Journal of Chemistry
%D 1969/09/01
%V 22
%N 9
%P 1975-1987
%K 
%R https://doi.org/10.1071/CH9691975
%U https://www.publish.csiro.au/paper/CH9691975 
%X Attempts have been made to effect fragmentation reactions with bromo- tetralone systems related to 6&#945;-bromo-13-hydroxytotara-8,11,13-trien-7- one (VII), a compound which affords a secoditerpenoid (IX) when treated with DMSO-NaHCO3. On treatment with sulphuric acid in acetone, the mono- epoxide derivative (XXVIII) of the methyl ether of the secoditerpenoid undergoes a novel aromatization to a naphthalenic aldehyde (XXXI) by successive transannular cyclization and fragmentation reactions.     A 7&#946;-hydroxy configuration has been confirmed for the major product from reduction of 13-acetoxytotara-8,11,13-trien-7-one (VIII) with lithium aluminium hydride. 13-Methoxytotara-8,11,13-triene (II) has been deisopropylated and then subjected to Birch reduction in an attempt to effect a high yield conversion into (+)-podocarp-8(14)-en- 13-one (XXXVII), a potentially useful intermediate for synthesis. 
