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Total Synthesis of Calystegine B 4
Author(s) -
Moosophon Panawan,
Baird Morwenna C.,
Kanokmedhakul Somdej,
Pyne Stephen G.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000157
Subject(s) - chemistry , total synthesis , metathesis , natural product , mannich reaction , salt metathesis reaction , combinatorial chemistry , ring closing metathesis , stereochemistry , product (mathematics) , organic chemistry , catalysis , polymerization , polymer , geometry , mathematics
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 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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