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Pheromone synthesis, CVI. Synthesis of all of the four stereoisomers of tetrahydro‐2,2,6‐trimethyl‐2 H ‐pyran‐3‐ol, a volatile compound from the elm bark beetle Pteleobius vittatus
Author(s) -
Mori Kenji,
Puapoomchareon Prapai
Publication year - 1988
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198819880212
Subject(s) - pyran , bark beetle , chemistry , bark (sound) , pheromone , stereochemistry , botany , biology , ecology
Abstract Oxymercuration of ( R )‐sulcatol ( 1 ) to (3 R ,6 R )‐ 2 was followed by its treatment with NaBH 4 and oxygen to give (3 S ,6 R )‐tetrahydro‐2,2,6‐trimethyl‐2 H ‐pyran‐3‐ol ( 3a ) and (3 R ,6 R )‐ 3a′ . In the same manner, (3 R ,6 S )‐ 3a and (3 S ,6 S )‐ 3a′ were synthesized from ( S )‐1.