Premium
Synthesis and Absolute Configuration at C(8) of ‘ p ‐Menthane‐3,8,9‐triol’ Derived from (–)‐Isopulegol
Author(s) -
Yuasa Yoshifumi,
Yuasa Yoko
Publication year - 2004
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.200490233
Subject(s) - chemistry , triol , absolute configuration , dihydroxylation , diastereomer , stereochemistry , diol , absolute (philosophy) , adduct , triethyl orthoformate , sharpless asymmetric dihydroxylation , organic chemistry , catalysis , enantioselective synthesis , philosophy , epistemology
Two diastereoisomers of the new, potentially insecticidal ‘ p ‐menthane‐3,8,9‐triol’ (=(2 S )‐ and (2 R )‐ 2‐[(1 R ,2 R ,4 R )‐2‐hydroxy‐4‐methylcyclohexyl]propane‐1,2‐diol; (8 S )‐ and (8 R )‐ 1 ), have been synthesized from (–)‐isopulegol by both conventional dihydroxylation and catalytic Sharpless dihydroxylation ( Scheme ). The absolute configuration at C(8) of the corresponding orthoformate adduct (8 S )‐ 3a was determined by 1 H‐NMR and X‐ray crystallographic analysis ( Figure ).