100906-45-4Relevant articles and documents
Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation Dedicated to Associated Professor Ladislav Knie?o on the occasion of his 70th birthday
Martinková, Miroslava,Mezeiová, Eva,Fabi?íková, Milica,Gonda, Jozef,Pilátová, Martina,Moj?i?, Ján
, p. 6 - 24 (2015)
Synthesis of the HCl salts of two anhydrophytosphingosines, jaspine B (1) and its 4-epi-congener 5 from easily available dimethyl l-tartrate and/or l-arabinose, is described. The key transformations are the efficient incorporation of a chiral amino group
Stereoselective syntheses and reactions of chiral oxygenated α,β-unsaturated-γ- and δ-lactones
Sanchez-Sancho, Francisco,Valverde, Serafin,Herradon, Bernardo
, p. 3209 - 3246 (2007/10/03)
The syntheses of the chiral α,β-unsaturated lactones (+)-5, (-)-6, (+)-8, (+)-9, and (+)-10 have been efficiently achieved from readily available starting materials. The lactone (+)-5 has been synthesized in 7 steps from (R,R)-dimethyl tartrate (38-43% overall yield). The use of (+)-5 in formal syntheses of natural (+)-asperlin 4 and advanced intermediates for (+)-olguine 2 are also reported. The lactone (-)-6 has been prepared in 5 steps from (R)-malic and (44-50% overall yield). It can be a useful precursor for the syntheses of branched chain and deoxy nucleoside analogues. The preparation of (-)-6 constitutes formal syntheses of natural (+)-eldanolide 53 and the (+)-Geissman-Waiss lactone 54 (an intermediate for the syntheses of a variety of pyrrolizidine alkaloids). The lactones (+)-8, (+)-9 and (+)-10 have been synthesized from 3,4-di-O-acetyl-L-rhamnal 58. The highly diastereoselective transformations of (+)-9 and (+)-10, through sequential conjugate nucleophilic addition and enolate reaction, into densely functionalized chiral γ-lactones 12 are also reported. Copyright (C) Elsevier Science Ltd.