Polyketide assembly by alkene-alkyne reductive cross-coupling: spiroketals through the union of homoallylic alcohols.
A reaction sequence composed of regioselective formal hydroalkynylation, reductive ene-yne cross-coupling, and oxidative cyclization has been developed to prepare stereochemically dense spiroketals. Overall, the chemistry defines a three-component coupling process for the union of two homoallylic alcohol-based substrates with trimethylsilylacetylene.
Canterbury
Daniel P
DP
Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA.
Micalizio
Glenn C
GC
D000438:Alcohols / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D000475:Alkenes; D000480:Alkynes; D005663:Furans; D013141:Spiro Compounds; C520774:spiroketal