
TY  - JOUR
A1  - Cambie, RC 
A1  - Crump, DR 
A1  - Duve, RN 
T1  - Chemistry of the Podocarpaceae. XXII. Aspects of the chemistry of Totara-8,11,13-trien-13-ol
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1969
VL  - 22
IS  - 9
SP  - 1975
EP  - 1987
KW  - 
UR  - https://doi.org/10.1071/CH9691975 
N2  - 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. 
ER  -

