An approach to lauroxanes by iterative use of Co(2)(CO)(6)-acetylenic complexes. a formal synthesis of (+)-laurencin.
A new approach to lauroxanes by a powerful and highly convergent methodology based on iterative use of Co(2)(CO)(6)-acetylenic complexes is described. The strategy employs an intermolecular Nicholas reaction to form unsaturated branched linear ethers, a ring closing metathesis to obtain the cobalt complex cyclic ethers, and an isomerization promoted by montmorillonite K-10. A short synthesis of cyclic ethers of seven-, eight-, and nine-membered rings is described. Additionally, the methodology is exemplified by the formal synthesis of (+)-laurencin, a red algae metabolite.
Ortega
Nuria
N
Departamento de Química Orgánica, Instituto Universitario de Bioorgánica Antonio González, Universidad de La Laguna, Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Islas Canarias, Spain.
Martín
Victor S
VS
Martín
Tomás
T
D000480:Alkynes / Q000737:chemistry*; D003035:Cobalt / Q000737:chemistry*; D003500:Cyclization; D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D035964:Oxocins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D005231:Fatty Acids, Unsaturated; D009942:Organometallic Compounds; D035964:Oxocins; C031203:2-hexadecynoic acid; C017460:laurencin; D003035:Cobalt