Hydroxyl-directed stereocomplementary pinacol cyclizations mediated by SmI2

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 479-480

  Kawatsura, M ^a   Kishi, E ^a   Kito, M ^a   Sakai, T ^a   Shirahama, H ^a,b   Matsuda, F ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002111615     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6153     Document Type: Article

References (21)

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9. 2) has become an exceedingly useful reagent for promoting the reductive coupling reactions in the last decade. For reviews, see: (a) Kagan, H.B. New J. Chem. 1990, 14, 453.
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12. The hydroxy keto-aldehyde l was prepared in 41% overall yield by a 3-step sequence of (1) the anti-selective aldol reaction of 4-(p-methoxyphenylmethoxy)butyraldehyde with the Li-enolate generated from (+)-dihydrocarvone, (2) the oxidative removal of the MPM group, and (3) selective oxidation with Dess-Martin periodinane.
13. 2 affected the efficient cyclization to the trans-decalin triols 2 and 3. Apparently, the hydroxy keto-aldehyde 1 must be generated during an equilibrium process before the pinacol coupling cyclizations.
14. 1-H).
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