Studies towards the total synthesis of halichlorine: asymmetric synthesis of the spiroquinolizidine subunit

Authors
Trauner, D Danishefsky, SJ
Citation
D. Trauner et Sj. Danishefsky, Studies towards the total synthesis of halichlorine: asymmetric synthesis of the spiroquinolizidine subunit, TETRAHEDR L, 40(36), 1999, pp. 6513-6516
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
36
Year of publication
1999
Pages
6513 - 6516
Database
ISI
SICI code
0040-4039(19990903)40:36<6513:STTTSO>2.0.ZU;2-H
Abstract
The C1-C15 spiroquinolizidine subunit (cf. 2) of the marine natural product halichlorine (1) was prepared in 12 steps starting from the known 'Meyers- lactam' 5. The synthesis involves a B-alkyl-Suzuki coupling followed by a h ighly stereoselective intramolecular Michael addition and an intramolecular Mannich ring closure. (C) 1999 Elsevier Science Ltd. All rights reserved.