An efficient synthesis of the C1–C19 segment of carolacton is described, starting
from d-ribose, (–)-β-citronellene and a homopropargylic alcohol, and which employs a Nozaki–Hiyama–Kishi
(NHK) coupling as the key step. Other important steps are cross-metathesis and Evans
aldol reactions.
Key words
carolacton - macrolide - Evans aldol - Nozaki–Hiyama–Kishi coupling - cross-metathesis