Asymmetric syntheses of lignans utilizing novel diastereoselective Michael addition of cyanohydrin: Syntheses of (+)-fargesin and (−)-picropodophyllone

The 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,...

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Published inTetrahedron Vol. 53; no. 28; pp. 9585 - 9598
Main Authors Yoshida, Shin-ichi, Yamanaka, Takeshi, Miyake, Tutomu, Moritani, Yasunori, Ohmizu, Hiroshi, Iwasaki, Tameo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.07.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIEQUATORIAL
LACTONES
DIASTEREOFACIAL SELECTION
DIFFERENT ARYL GROUPS
EQUATORIAL FUROFURAN LIGNANS
ACETONIDE
NEOLIGNANS
STEREOCONTROLLED SYNTHESIS
(-)-PODOPHYLLOTOXIN
STEREOSELECTIVE REACTIONS
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Summary:The 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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)00643-1