Asymmetric syntheses of lignans utilizing novel diastereoselective Michael addition of cyanohydrin: Syntheses of (+)-fargesin and (−)-picropodophyllone
1997; Elsevier BV; Volume: 53; Issue: 28 Linguagem: Inglês
10.1016/s0040-4020(97)00643-1
ISSN1464-5416
AutoresShin�ichi Yoshida, Takeshi Yamanaka, T. Miyake, Yasunori Moritani, Hiroshi Ohmizu, Tameo Iwasaki,
Tópico(s)Phytochemistry and Biological Activities
ResumoThe Michael addition reaction of lithium salt of cyanohydrin to (S)- and (R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-cis-2-propenoate (2 and 3) proceeded in 93% de in the presence of two equivalents of HMPA at −100 °C. This diastereoselectivity could be elucidated by the stereocontrol based on the 1,3-allylic strain. Utilizing this reaction, stereocontrolled syntheses of (+)-fargesin (6) and (−)-picropodophyllone (7) were achieved.
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