Enantioselective total synthesis of (+)-rogioloxepane A.
[reactiojn: see text] The enantioselective synthesis of (+)-rogioloxepane A has been achieved in 21 steps from 1,5-hexadien-3-ol. The key steps in the synthesis are an asymmetric glycolate alkylation leading to the diene 2 and a subsequent ring-closing metathesis to construct the oxepene core.
Crimmins
Michael T
MT
Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA. crimmins@email.unc.edu
DeBaillie
Amy C
AC
D000466:Alkadienes / Q000737:chemistry; D000478:Alkylation; D006016:Glycolates / Q000737:chemistry; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry; D000461:Rhodophyta / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; D006016:Glycolates; D010082:Oxepins; C478288:rogioloxepane A