Synthesis and Absolute Configuration at C(8) of ‘p‐Menthane‐3,8,9‐triol’ Derived from (–)‐Isopulegol |
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| Authors: | Yoshifumi Yuasa Yoko Yuasa |
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| Institution: | 1. Takasago International Corporation, 1-5-1 Nishiyawata, Hiratsuka, Kanagawa, 254-0073, Japan (phone: 81-(0)463-21-7516;2. fax: 81-(0)463-21-7413);3. School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, 192-0392, Tokyo, Japan |
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| Abstract: | Two diastereoisomers of the new, potentially insecticidal ‘p‐menthane‐3,8,9‐triol’ (=(2S)‐ and (2R)‐ 2‐(1R,2R,4R)‐2‐hydroxy‐4‐methylcyclohexyl]propane‐1,2‐diol; (8S)‐ and (8R)‐ 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 (8S)‐ 3a was determined by 1H‐NMR and X‐ray crystallographic analysis (Figure). |
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