Citation
Xt. Chen et al., The total synthesis of eleutherobin, J AM CHEM S, 121(28), 1999, pp. 6563-6579
Citations number
83
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN journal
00027863
→ ACNP
Volume
121
Issue
28
Year of publication
1999
Pages
6563 - 6579
Database
ISI
SICI code
0002-7863(19990721)121:28<6563:TTSOE>2.0.ZU;2-Z
Abstract
The total synthesis of the title compound (1), starting with (R)-(-)-alpha-
phellandrene (6), has been accomplished. The synthesis rigorously proves th
e relative stereochemical relationship of the diterpenoid and carbohydrate
domains of eleutherobin. Key reactions included a Nozaki-Kishi ring closure
to produce a furanophane (see 37 --> 38), a pyranose to furanose transposi
tion (see 50 --> 47), and a novel oxycarbaglycosidation (cf. 58 --> 87) for
joining the two domains.