Polyhydroxylated pyrrolizidines. Part 1: Short and highly stereocontrolledsyntheses of hyacinthacines

Authors
Izquierdo, I Plaza, MT Robles, R Franco, F
Citation
I. Izquierdo et al., Polyhydroxylated pyrrolizidines. Part 1: Short and highly stereocontrolledsyntheses of hyacinthacines, TETRAHEDR-A, 12(17), 2001, pp. 2481-2487
Citations number
15
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
17
Year of publication
2001
Pages
2481 - 2487
Database
ISI
SICI code
0957-4166(20010928)12:17<2481:PPP1SA>2.0.ZU;2-0
Abstract
Two short and highly stereocontrolled syntheses for 7a-epi-hyacinthacine A( 2) (7-deoxyalexine) 3 and 5,7a-diepihyacinthacine A(3) 4 are, respectively, reported herein. An appropriately protected polyhydroxypyrrolidine. (2R,3R ,4R,5S)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2, 5-bis(hydroxymethyl)pyrrolidine 5, readily available from D-fructose, was c hosen as the chiral starting material. (C) 2001 Elsevier Science Ltd. All r ights reserved.