Stereodivergent and Regioselective Synthesis of 3,4-cis- and 3,4-trans-Pyrrolidinediols from α-Amino Acids
- 1 June 2004
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (13), 2273-2276
- https://doi.org/10.1021/ol049237g
Abstract
[reaction: see text] Highly stereodivergent Woodward-Prevost reaction applied to iodoacetates derived from homochiral alpha-amino acids afforded enantiopure 3,4-cis- and 3,4-trans-pyrrolidinediol derivatives, with control over the protecting group, allowing for differential protection.Keywords
This publication has 19 references indexed in Scilit:
- Diastereoselective iodoamidation of 3-acetyloxybut-1-enylamines: simple synthesis of a precursor of aza sugars involving a pyrrolidine ringChemical Communications, 1999
- The Efficient, Enantioselective Synthesis of Aza Sugars from Amino Acids. 1. The Polyhydroxylated PyrrolidinesThe Journal of Organic Chemistry, 1997
- Woodward−Prevost Reactions of 1,7-Dioxaspiro[5.5]undec-4-enesThe Journal of Organic Chemistry, 1996
- Stereoselective Synthesis of β‐Amino Alcohols from Optically Active α‐Amino AcidsAngewandte Chemie International Edition in English, 1987
- INHIBITORS OF THE BIOSYNTHESIS AND PROCESSING OF N-LINKED OLIGOSACCHARIDE CHAINSAnnual Review of Biochemistry, 1987
- .alpha.-Amino acids as chiral educts for asymmetric products. Chirospecific syntheses of methyl L-sibirosaminide and its C-3 epimer from L-allothreonineThe Journal of Organic Chemistry, 1985
- Steroids and related natural products. 93. Bufadienolides. 30. Synthesis of the Ch'an Su component 15.beta.-hydroxybufalinThe Journal of Organic Chemistry, 1975
- Isolation and characterization of a l-pyrindine fungal alkaloidJournal of the American Chemical Society, 1973
- cis-Hydroxylation of a Synthetic Steroid Intermediate with Iodine, Silver Acetate and Wet Acetic AcidJournal of the American Chemical Society, 1958
- ANISOMYCIN,1 A NEW ANTI-PROTOZOAN ANTIBIOTICJournal of the American Chemical Society, 1954