Bioscience, Biotechnology and Biochemistry p. 1453 - 1462 (1999)
Update date:2022-08-03
Topics:
Yamauchi, Satoshi
Machi, Mitsuo
Kinoshita, Yoshiro
(-)-Podorhizol (1) was stereoselectively synthesized by erythro preferential aldol condensation of 3,4,5-trimethoxybenzaldehyde with potassium enolate from (+)-(R)-3-(3,4-methylenedioxybenzyl)-4-butanolide (2) (erythro: threo=85:15). Erythro selectivity was observed in the aldol condensation of many alkoxybenzaldehydes with potassium enolate from (+)-γ-butyrolactone 2. However, benzaldehydes having methoxy groups at both the 2 and 6 positions gave threo selectivity in the aldol condensation with potassium enolate from (+)-γ-butyrolactone 2.
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Doi:10.1002/ejoc.201601300
(2017)Doi:10.1007/BF00909445
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