Total synthesis of calystegine B4

Authors

Panawan Moosophon, University of Wollongong
Morwenna C. Baird, University of Wollongong
Somdej Kanokmedhakul, University of Khon Kaen
Stephen G. Pyne, University of WollongongFollow

RIS ID

33459

Publication Details

Moosophon, P., Baird, M. C., Kanokmedhakul, S. & Pyne, S. G. (2010). Total synthesis of calystegine B4. European Journal of Organic Chemistry, 2010 (17), 3337-3344.

Abstract

The total synthesis of calystegine B₄ was achieved in 10 steps from (–)-D-lyxose by using a new synthetic strategy to obtain the requisite protected hydroxylated 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.