Development of organoiron methodology for preparation of the polyene natural product macrolactin A

Authors
Barmann, H Prahlad, V Tao, CL Yun, YK Wang, Z Donaldson, WA
Citation
H. Barmann et al., Development of organoiron methodology for preparation of the polyene natural product macrolactin A, TETRAHEDRON, 56(15), 2000, pp. 2283-2295
Citations number
48
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
15
Year of publication
2000
Pages
2283 - 2295
Database
ISI
SICI code
0040-4020(20000407)56:15<2283:DOOMFP>2.0.ZU;2-2
Abstract
Methodology for the synthesis of the C7-C13 segment (19) and C14-C24 segmen t (41) of macrolactin A have been developed. Dicarbonyl(methyl 7-nitro-2E,4 Z-heptadienoate)triphenylphosphineiron (19) is prepared by nucleophilic add ition to a (1-methoxycarbonylpentadienyl)iron cation. The C23 stereocenter of 41 is established by introduction of a C20 stereocenter, chirality trans fer from C20 to C23 followed by (diene)iron mediated selective ionic reduct ion of the C20 hydroxyl. The C15 stereocenter may be established by nitrile oxide-olefin cyclocondensation. (C) 2000 Elsevier Science Ltd. All rights reserved.