642486-86-0Relevant academic research and scientific papers
Formal Total Synthesis of (+)-Salicylihalamides A and B: A Combined Chiral Pool and RCM Strategy
Yang, KyoungLang,Blackman, Burchelle,Diederich, Wibke,Flaherty, Patrick T.,Mossman, Craig J.,Roy, Subho,Ahn, Yu Mi,Georg, Gunda I.
, p. 10030 - 10039 (2003)
The formal total synthesis of the (+)-salicylihalamides A and B is detailed, utilizing a chiral pool approach to generate the three stereogenic centers and a ring-closing metathesis (RCM) for the formation of the macrocyclic ring structure. Starting from a known glucose-derived alcohol, the formal total synthesis was achieved in an efficient 13-step protocol in 26% overall yield. It was found that substitution at the remote phenolic group significantly influenced the ratio of the E-and Z-double bond products in the RCM step. The introduction of phenol protecting groups provided E-isomers preferentially and also enhanced the rates of the RCM reactions.
