Convenient One-Pot Synthesis of Spiro- (E) -?-Ethylidene-?-Butyrolactones
- 1 January 1984
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 14 (1) , 11-20
- https://doi.org/10.1080/00397918408060858
Abstract
Treatment of the di-anion (5) derived from N, 2-dimethyl-2-(E), -butenamide (4) with cycloalkanones, followed by acid-catalysed hydrolysis and cyclodehydration of the resulting adducts, in a ‘one-pot’ procedure, provides a convenient stereospecific synthesis of spiro-(E), -α-ethylidene-γ-butyrolactones, e.g., (6), (7), and (9).Keywords
This publication has 13 references indexed in Scilit:
- .beta.' Metalation of .alpha.,.beta.-unsaturated tertiary amidesThe Journal of Organic Chemistry, 1982
- A short stereoselective synthesis of (±)-litsenolides C1 and C2.Tetrahedron Letters, 1982
- Stereochemistry of deconjugative alkylation of ester dienolates. Stereospecific total synthesis of the litsenolidesThe Journal of Organic Chemistry, 1982
- Total synthesis of Lauraceae lactones: obtusilactones, litsenolides, and mahubanolidesJournal of the American Chemical Society, 1981
- .beta.'-Lithiation of .alpha.,.beta.-unsaturated secondary amidesJournal of the American Chemical Society, 1980
- Synthesis of (±)-litsenolide ClTetrahedron Letters, 1980
- Alkylation of α,β-unsaturated amides metalated and dimetalated intermediatesTetrahedron Letters, 1978
- Isolation and structural elucidation of allamandin, and antileukemic iridoid lactone from allamanda catharticaThe Journal of Organic Chemistry, 1974
- Components of the Lauraceae family—ITetrahedron, 1972
- Über die Struktur von Plumericin, Isoplumericin, β‐Dihydroplumericin und der β‐DihydroplumericinsäureHelvetica Chimica Acta, 1961