Versatile synthetic method for sphingolipids and functionalized sphingosine derivatives via olefin cross metathesis

T Yamamoto, H Hasegawa, T Hakogi… - Organic Letters, 2006 - ACS Publications
T Yamamoto, H Hasegawa, T Hakogi, S Katsumura
Organic Letters, 2006ACS Publications
A highly efficient and versatile method for the synthesis of various sphingolipids, such as
sphingomyelin, ceramide, sphingosine, sphingosine 1-phosphate, and functionalized
sphingosine derivatives, was established by two types of combinations of the olefin cross
metathesis reaction. One reaction was between the same olefin part and appropriate amino
alcohols, which were prepared starting from N-Boc-l-serine, and the other was between
appropriate olefins and the same amino alcohol.
A highly efficient and versatile method for the synthesis of various sphingolipids, such as sphingomyelin, ceramide, sphingosine, sphingosine 1-phosphate, and functionalized sphingosine derivatives, was established by two types of combinations of the olefin cross metathesis reaction. One reaction was between the same olefin part and appropriate amino alcohols, which were prepared starting from N-Boc-l-serine, and the other was between appropriate olefins and the same amino alcohol.
ACS Publications