Chemistry Letters p. 179 - 180 (1995)
Update date:2022-07-31
Topics:
Mukaiyama, Teruaki
Shiina, Isamu
Sakata, Kaku
Emura, Takayuki
Seto, Keitarou
Saitoh, Masahiro
Optically active 3,7-dibenzyloxy-4,8-di-t-butyldimethylsiloxy-5,5-dimethyl-6-p-methoxybenzyloxy-2-octanone (2) has been synthesized by way of diastereoselective aldol reaction between 4-benzyloxy-5-t-butyldimethylsiloxy-2,2-dimethyl-3-p-methoxy-benzyloxypentanal (3) and ketene silyl acetal 4 using MgBr2*OEt2 as a catalyst.The chiral pentanal 3 was synthesized either by asymmetric aldol reaction of both prochiral aldehyde 5 and ketene silyl acetal 4 using a chiral Lewis acid or by diastereoselective aldol reaction between the chiral aldehyde 6 derived from L-serine andthe lithium enolate derived from methyl isobutyrate.
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