page_title: Totarol
section_title: Synthesis
hierarchical_section_title: Totarol / Synthesis
context_page_description: Totarol is a naturally produced diterpene that is bioactive as-totarol. It was first isolated by McDowell and Esterfield from the heartwood of Podocarpus totara, a yew tree found in New Zealand. Podocarpus totara was investigated for unique molecules due to the tree's increased resistance to rotting. Recent studies have confirmed-totarol's unique antimicrobial and therapeutic properties. Consequently, -totarol is a promising candidate for a new source of drugs and has been the goal of numerous syntheses.
context_section_description: (+)-Totarol has been the subject of numerous syntheses.  The first total synthesis of totarol (Scheme 3) utilized 6 and the alkyne 7 to yield 8 which was converted to the corresponding ketone 9 via hydrogenation followed by cyclization with polyphosphoric acid. 9 was subsequently converted to 10 and another ketone that were inseparable by chromatography. The synthesis was finalized by treatment of with N-Bromosuccinimide followed by debromination to yield (±)-totarol. The main downfall of this synthesis was that in multiple steps, complete conversion of reactant to products was not observed and undesirable side products were often not separable by chromatography. However, since this was the first total synthesis of (±)-totarol, it is notable.
caption: Scheme 3. The first total synthesis of (±)-totarol