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Vitamin‐B 12 ‐Catalyzed C,C‐Bond Formation. Synthesis of a california red scale pheromone
Author(s) -
Auer Lucas,
Weymuth Christophe,
Scheffold Rolf
Publication year - 1993
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19930760205
Subject(s) - chemistry , catalysis , acetal , ethylene , stereochemistry , pheromone , organic chemistry , botany , biology
A Mixture of (3 S ,6 R )‐ and (3 R ,6 R )‐3‐methyl‐6‐(1‐methylethenyl)dec‐9‐enyl acetate ( 1a and 1b , respectively)– 1a being a pheromone of the California red scale – is synthesized in 14 steps from (+)‐( R )‐limonene ( 4 ). The key step is the reductive vitamin‐ B 12 ‐catalyzed coupling of ( R )‐5‐(2‐iodoethyl)‐6‐mehtylhept‐6‐en‐2‐one ethylene acetal ( 8 ) and methyl crotonate ( 3 ).