European Journal of Organic Chemistry, volume 2010, issue 17, pages 3337-3344
Total Synthesis of Calystegine B4
Panawan Moosophon
1
,
Morwenna C Baird
2
,
Somdej Kanokmedhakul
3
,
Stephen J. Pyne
2
2
School of Chemistry, Univ. of Wollongong, Wollongong, NSW 2522, Australia
|
3
Department of Chemistry, University of Khon Kaen, Khon Kaen 40002, Thailand
|
Publication type: Journal Article
Publication date: 2010-05-04
scimago Q2
SJR: 0.584
CiteScore: 5.4
Impact factor: 2.5
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
The total synthesis of calystegine B 4 was achieved in 10 steps from (―)-D-lyxose by using a new synthetic strategy to obtain the requisite protected hydroxylacted 4-aminocyclohept-2-en-1-one without the problem of regioisomer formation that was a problem in the earlier synthesis of this natural product. The key steps included a Petasis―borono-Mannich reaction and a ring-closing metathesis reaction.
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