Article

Combined coinage metal catalysis in natural product synthesis: total synthesis of (+)-varitriol and seven analogs.

Organic Chemistry, Dortmund University of Technology, D-44227-Dortmund, Germany.
Organic & Biomolecular Chemistry (impact factor: 3.7). 03/2012; 10(30):5965-70. DOI:10.1039/c2ob25069a pp.5965-70
Source: PubMed

ABSTRACT A modular total synthesis of the natural product (+)-varitriol (1) and seven analogs was achieved by using combined coinage metal catalysis. Starting from enynol 13, reagent-controlled introduction of stereogenic centers and efficient center-to-axis-to-center chirality transfer viaα-hydroxyallene 5 afforded (+)-varitriol with 6.4% yield over 10 steps.

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Keywords

coinage metal catalysis
 
efficient center-to-axis-to-center chirality transfer viaα-hydroxyallene 5
 
enynol 13
 
natural product
 
stereogenic centers