Enantioselective synthesis of macrocyclic propargylic alcohols by [2,3] Wittig ring contraction. Synthesis of (+)-aristolactone and cembranoid precursors

1988 ◽  
Vol 110 (9) ◽  
pp. 2925-2931 ◽  
Author(s):  
James A. Marshall ◽  
Jacques. Lebreton
Keyword(s):  
Enantioselective Synthesis ◽  
Ring Contraction ◽  
Propargylic Alcohols

Enantioselective Synthesis of Tertiary Propargylic Alcohols under N-Heterocyclic Carbene Catalysis

2015 ◽  
Vol 21 (23) ◽  
pp. 8384-8388 ◽  
Author(s):  
Eduardo Sánchez-Díez ◽  
Maitane Fernández ◽  
Uxue Uria ◽  
Efraim Reyes ◽  
Luisa Carrillo ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Propargylic Alcohols

scholarly journals 8-Step Enantiodivergent Synthesis of (+)- and (-)-Lingzhiol

2019 ◽  
Author(s):  
Paul S. Riehl ◽  
Alistair D. Richardson ◽  
Tatsuhiro Sakamoto ◽  
Corinna Schindler
Keyword(s):  
Natural Product ◽  
Michael Reaction ◽  
Secondary Alcohol ◽  
Enantioselective Synthesis ◽  
Ring Contraction ◽  
Metal Source ◽  
Benzylic Oxidation ◽  
Asymmetric Michael Reaction

<div> <div> <p>An 8-step enantioselective synthesis of lingzhiol is described herein. The sense of an asymmetric Michael reaction is reversed by the choice of metal source, enabling facile access to both enantiomers. A spontaneous semipinacol ring contraction enables mild construction of the lingzhiol core, and radical-mediated benzylic oxidation proceeds in the presence of an unprotected secondary alcohol. This represents the shortest enantioselective synthesis of lingzhiol to date, and the only enantiodivergent approach to both enantiomers of this meroterpenoid natural product.</p> </div> </div>

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