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Synthesis and Absolute Configuration at C(8) of ‘p-Menthane-3,8,9-triol’ Derived from (–)-Isopulegol

✍ Scribed by Yoshifumi Yuasa; Yoko Yuasa

Publisher: John Wiley and Sons
Year: 2004
Tongue: German
Weight: 127 KB
Volume: 87
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200490233

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✦ Synopsis

Abstract

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).

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