A concise enantioselective synthesis of the AB ring system of the manzamine alkaloids by ring-closing enyne metathesis

Authors
Clark, JS Townsend, RJ Blake, AJ Teat, SJ Johns, A
Citation
Js. Clark et al., A concise enantioselective synthesis of the AB ring system of the manzamine alkaloids by ring-closing enyne metathesis, TETRAHEDR L, 42(18), 2001, pp. 3235-3238
Citations number
55
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
18
Year of publication
2001
Pages
3235 - 3238
Database
ISI
SICI code
0040-4039(20010430)42:18<3235:ACESOT>2.0.ZU;2-N
Abstract
The AB ring system found in the manzamine A and related alkaloids has been prepared from (-)-quinine by a short enantioselective route. The key step i n the sequence is a ruthenium-catalysed ring-closing enyne metathesis re ac tion which delivers a bicyclic diene in good yield. The functionality requi red for further elaboration of the AB system has been installed by sequenti al regioselective hydroboration and stereoselective catalytic aminohydroxyl ation. (C) 2001 Elsevier Science Ltd. AH rights reserved.