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-en1-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. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.