Title

Total synthesis of calystegine B4

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.

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Link to publisher version (DOI)

http://dx.doi.org/10.1002/ejoc.201000157