TOTAL SYNTHESIS OF THE CYTOTOXIC ANNONACEOUS ACETOGENIN (30S)-BULLANIN

Authors
MARSHALL JA HINKLE KW
Citation
Ja. Marshall et Kw. Hinkle, TOTAL SYNTHESIS OF THE CYTOTOXIC ANNONACEOUS ACETOGENIN (30S)-BULLANIN, Tetrahedron letters, 39(11), 1998, pp. 1303-1306
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
11
Year of publication
1998
Pages
1303 - 1306
Database
ISI
SICI code
0040-4039(1998)39:11<1303:TSOTCA>2.0.ZU;2-4
Abstract
The total synthesis of (+)-(30S)-bullanin, a highly cytotoxic Annonace ous acetogenin, was effected by a convergent approach in which the key core bis-2,2'-tetrahydrofuran stereocenters were introduced through a combination of Sharpless asymmetric dihydroxylation and S(E)2' additi ons of oxygenated nonracemic allylic stannane and indium reagents to g amma-oxygenated aldehydes. (C) 1998 Elsevier Science Ltd. All rights r eserved.