IMDA/aldol strategy for transforming carbohydrates into functionalized trans-decalins
Corresponding Author
Bert Fraser-Reid
Natural Products and Glycotechnology Research Institute, Inc., Durham, North Carolina
Natural Products and Glycotechnology Research Institute, Inc., 4118 Swarthmore Road, Durham, NC 27707 USASearch for more papers by this authorXiao-Tao Chen
Department of Chemistry, Duke University, Durham, North Carolina
Search for more papers by this authorDieter Haag
Natural Products and Glycotechnology Research Institute, Inc., Durham, North Carolina
Search for more papers by this authorKenneth J. Henry Jr.
Department of Chemistry, Duke University, Durham, North Carolina
Search for more papers by this authorAndrew T. McPhail
Department of Chemistry, Duke University, Durham, North Carolina
Search for more papers by this authorCorresponding Author
Bert Fraser-Reid
Natural Products and Glycotechnology Research Institute, Inc., Durham, North Carolina
Natural Products and Glycotechnology Research Institute, Inc., 4118 Swarthmore Road, Durham, NC 27707 USASearch for more papers by this authorXiao-Tao Chen
Department of Chemistry, Duke University, Durham, North Carolina
Search for more papers by this authorDieter Haag
Natural Products and Glycotechnology Research Institute, Inc., Durham, North Carolina
Search for more papers by this authorKenneth J. Henry Jr.
Department of Chemistry, Duke University, Durham, North Carolina
Search for more papers by this authorAndrew T. McPhail
Department of Chemistry, Duke University, Durham, North Carolina
Search for more papers by this authorAbstract
L-Rhamnal is readily converted into an allyl 2,3-unsaturated-C-glycopyranoside. The (S) configuration of the αL-anomer defines the stereochemical outcome of the future IMDA reaction, leading to the absolute stereochemistry for the trans-decalin moiety in naturally occurring terpenoids. Selective cleavage of the terminal double bond of the allyl group provides an aldehydo function which serves for an aldol/Claisen addition with ethyl sorbate. Of the four possible diastereomers, one is obtained in pure form and processed to give the IMDA precursor. Cyclocondensation is achieved by heating in xylene to give a tricyclic trans-decalin whose structure is established by NMR and X-ray analysis. Chirality 12:488–495, 2000. © 2000 Wiley-Liss, Inc.
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